3-(Boc-amino)-L-alanine → N-[(4-{(2S)-3-(Allyloxy)-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl}phenoxy)carbonyl]-3-[(tert-butoxycarbonyl)amino]-L-alanine

HRID 630669노트

반응식

HRID 630669 반응식
[CH2:1]([O:4][C:5](=[O:35])[C@H:6]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23](OC2C=CC([N+]([O-])=O)=CC=2)=[O:24])=[CH:18][CH:17]=1)[NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:2]=[CH2:3].[C:36]([O:40][C:41]([NH:43][CH2:44][C@@H:45]([C:47]([OH:49])=[O:48])[NH2:46])=[O:42])([CH3:39])([CH3:38])[CH3:37]>ClC(Cl)C>[CH2:1]([O:4][C:5](=[O:35])[C@@H:6]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]([NH:46][C@H:45]([C:47]([OH:49])=[O:48])[CH2:44][NH:43][C:41]([O:40][C:36]([CH3:39])([CH3:37])[CH3:38])=[O:42])=[O:24])=[CH:18][CH:17]=1)[CH:2]=[CH2:3]

참가 물질

4

반응물 2

HCID 103528593-(Boc-amino)-L-alanineHCID 117612078Allyl-N-(tert-butoxycarbonyl)-O-[(4-nitrophenoxy)carbonyl]-L-tyrosinate

생성물 1

HCID 89544774N-[(4-{(2S)-3-(Allyloxy)-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl}phenoxy)carbonyl]-3-[(tert-butoxycarbonyl)amino]-L-alanine

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

반응 조건

온도
85 °C

실험 절차

2.45 g (5.0 mmol) of the compound from example 1A was dissolved in 40 ml dichloroethane. 1.03 g, (5.0 mmol) 3-[(tert-Butoxycarbonyl)amino]-L-alanine was added. The reaction mixture was heated to 85° C. for 2 h. The solvent was removed under reduced pressure. The raw product was dissolved in dichloromethane and chromatographed over approx. 150 ml silica gel. Solvents used were dicloromethane/methanol 20/1 to dichloromethane/methanol 1/1. The product-containing fractions were combined and concentrated to dryness under reduced pressure. This gave 1.23 g (2.2 mmol, 44% of theory) of the desired product.

후처리

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe raw product was dissolved in dichloromethane
  3. customchromatographed over approx. 150 ml silica gel
  4. concentrationconcentrated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-9ec7729c2bf64559bfa316e99d8bb6c2
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315543B2

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