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 630669ノート

反応式

HRID 630669 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9ec7729c2bf64559bfa316e99d8bb6c2
出典データセット
uspto-grants-2016_04
特許番号
US09315543B2

反応ノート

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