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KR900011711A - 이소프로필 3s-아미노-2r-히드록시-알카노에이트의 제조방법 및 그의 중간체 - Google Patents

이소프로필 3s-아미노-2r-히드록시-알카노에이트의 제조방법 및 그의 중간체 Download PDF

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KR900011711A
KR900011711A KR1019900000567A KR900000567A KR900011711A KR 900011711 A KR900011711 A KR 900011711A KR 1019900000567 A KR1019900000567 A KR 1019900000567A KR 900000567 A KR900000567 A KR 900000567A KR 900011711 A KR900011711 A KR 900011711A
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웨인 더거 로버트
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Abstract

내용 없음

Description

이소프로필 3S-아미노-2R-히드록시-알카노에이트의 제조방법 및 그의 중간체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (12)

  1. 하기 일반식(X)의 절대 입체화학적 구조를 갖는 화합물.
    (X)
    식 중, R은 페닐, 이소프로필 또는 시클로헥실기이고, X,Y 및 Z는 각각 (A) 첫번째 경우에 있어서, Z는이고, 이때 R1은 (C1-C4)알킬 또는 페닐기이며, X 및 Y는 함께 환상 무수물형성하거나, 또는 X 및 Y는 독립적으로, X는 -O-CH(CH3)2기를 나타내고, Y는〔여기서, R2는 (C2-C4) 알콕시 카르보닐, 페녹시카르보닐 또는 벤질옥시카르보닐기를 나타냄〕,또는NH-기를 나타내며, (B) 두번째 경우에 있어서, Z는 수소 원자를 나타내며, X는 -OH이고, Y는이거나, 또는 X는 -O-CH(CH3)2기를 나타내고, Y는 (CH3)2CHO기 또는 -NH2기를 나타내며, 다만 Y가 NH2기일때, R은 페닐기이다.
  2. 제1항에 있어서, R1이 메틸기인 첫번째 경우의 화합물.
  3. 제2항에 있어서, R이 페닐기인 화합물.
  4. 제2항에 있어서, R이 이소프로필기인 화합물.
  5. 제2항에 있어서, R이 시클로헥실기인 화합물.
  6. 제1항에 있어서, 두번째 경우의 화합물.
  7. 제6항에 있어서, R이 페닐기인 화합물.
  8. 제6항에 있어서, R이 이소프로필기인 화합물.
  9. 제6항에 있어서, R이 시클로헥실기인 화합물.
  10. (a) 하기 일반식(Ⅱ)의 2R, 3S- 말산 유도체를 과량의 구조식 R1COC1의 산 염화물 또는 구조식(R1CO)2O의 무수물〔식중, R1은 (C1-C4)알킬 또는 페닐기임〕과 반응시켜 하기 일반식(Ⅲ)의 환상 무수물을 형성하고, (b) 생성된 일반식(Ⅲ)의 환상 무수물을 과량의 이소프로판올과 반응시켜 하기 일반식(Ⅳ)의 헤미에스테르를 형성하고, (c) 생성된 일반식(Ⅳ)의 헤미 에스테르의 카르복실산 기를 활성화시키고, 이 활성화된 형태의 산을 암모니아와 반응시켜 하기 일반식(Ⅳ)의 에스테르-아미드를 형성하고, (d) 생성된 일반식(Ⅵ)의 에스테르-아미드를 t-부탄올 중의 Pb(OCOCH3)4의 작용에 의하여 재배열시켜, 하기 일반식(Ⅶ)의 t-부틸옥시카르보닐아미노 에스테르를 형성하고, (e) 생성된 일반식(Ⅶ)의 t-부틸옥시카르보닐아미노 에스테르를 산촉매 존재하에 이소프로판올로가용매분해 시켜 하기 일반식(I)의 이소프로필 3S-아미노-2R-히드록시 알카노에이트를 형성하는 하기 일반식(I)의 화합물의 단계식 제조 방법.
    (I)
    (II)
    (III)
    (IV)
    (VI)
    (VII)
    상기 식 중, R은 페닐, 이소프로필 또는 시클로헥실기를 나타내고, R1은 (C1-C4)알킬 또는 페닐기를 나타낸다.
  11. 제10항에 있어서, R이 페닐기인 경우, 추가로 R이 페닐기인 일반식(I)의 이소프로필 3S-아미노-2R-히드록시-4-페닐 부틸레이트를 로듐 촉매 상에서 수소 첨가 반응시키는 것을 특징으로 하는 R이 시클로헥실기인 일반식(I)의 이소프로필 3S-아미노-4-시클로헥실-2R-히드록시 부틸레이트의 제조방법.
  12. 제10항에 있어서, 추가로(I) R-말산을 산 촉매 존재하에 과량의 이소프로판올로 에스테르화시켜 디이소프로필 R-말레이트를 형성하고, (Ⅱ) 상기 다이소프로필 말레이트를 강염기의 작용에 의하여 에놀레이트로 전환시키고, R이 페닐기일 때, (Ⅲ) 상기 에놀이트를 벤질화제와 반응시켜 디이소프로필 2R-히드록시-3S-(페닐메틸) 부탄디오에이트를 형성하거나, 또는 R이 이소프로필기일 때, (IV)상기 에놀레이트를 메탈릴화제와 반응시켜 다이소프로필 2R-히드록시-3S-(2-메틸-2-프로페닐) 부탄 디오에이트를형성한 후, 이어서 수소 첨가 반응시켜 디이소프로필 2R-히드록시-3S-(이소부틸)부탄디오에이트를 제조하고, (V) 상기 페닐메틸 또는 이소부틸 부탄디오에이트 에스테르를 물 및 염기성 촉매 존재하에 가수분해시켜 R이 페닐 또는 이소프로필기인 일반식(Ⅱ)의 2R, 3S-말산 유도체를 형성하고, 또한 R이 시클로헥실기일 때, (Ⅵ) R이 페닐기인 일반식(Ⅱ)의 상기 2R,3S-말산 유도체를 로듐 촉매 상에서 수소 첨가 반응시켜 R이 시클로헥실기인 일반식(Ⅱ)의 2R,3S-말산 유도체를 형성하는 연속 공정에 의해 일반식(Ⅱ)의 2R,3S-말산 유도체를 제조하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019900000567A 1989-01-19 1990-01-18 이소프로필 3s-아미노-2r-히드록시-알카노에이트의 제조 방법 및 그의 중간체 Expired - Fee Related KR940000197B1 (ko)

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US29986389A 1989-01-19 1989-01-19
US299,863 1989-01-19
US07/374,200 US4965372A (en) 1989-01-19 1989-06-29 Process and intermediates for isopropyl 3S-amino-2R-hydroxy-alkanoates
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AU611603B2 (en) 1991-06-13
FI900292A0 (fi) 1990-01-18
ES2062317T3 (es) 1994-12-16
EP0379288A1 (en) 1990-07-25
NO900261L (no) 1990-07-20
DE69005317D1 (de) 1994-02-03
ATE98953T1 (de) 1994-01-15
NO900261D0 (no) 1990-01-18
AU4856890A (en) 1990-07-26
FI900292A7 (fi) 1990-07-20
IE61797B1 (en) 1994-11-30
PT92879A (pt) 1990-07-31
EP0379288B1 (en) 1993-12-22
JPH02229134A (ja) 1990-09-11
DK0379288T3 (da) 1994-04-11
US4965372A (en) 1990-10-23
MY104896A (en) 1994-06-30
CA2007906A1 (en) 1990-07-19
NZ232153A (en) 1991-09-25
KR940000197B1 (ko) 1994-01-12
DE69005317T2 (de) 1994-04-28
IL93039A0 (en) 1990-11-05

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