Phthalimide → tert-butyl-2(R)-[(tert-butoxycarbonyl)amino]-3-phthalimidopropionate

HRID 1760806ノート

反応式

HRID 1760806 の反応式
[C:1]([O:5][CH2:6][C@H:7]([C:16](O)=O)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2].[C:19]1(=[O:29])[NH:23][C:22](=[O:24])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=[O:52]>O1CCCC1>[C:1]([O:5][C:6](=[O:52])[C@H:7]([NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:16][N:23]1[C:19](=[O:29])[C:20]2=[CH:28][CH:27]=[CH:26][CH:25]=[C:21]2[C:22]1=[O:24])([CH3:2])([CH3:3])[CH3:4]

参加物

6

反応物 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 6992546(R)-3-(tert-Butoxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

生成物 1

HCID 18337585tert-butyl-2(R)-[(tert-butoxycarbonyl)amino]-3-phthalimidopropionate収率 62.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of O-tert-butyl-N-BOC-D-serine (4 g, 15.31 mmol), phthalimide (3.38 g, 22.9 mmol) and triphenyl phosphine (6.03 g, 22.9 mmol) in tetrahydrofuran (120 ml, anhydrous) was added diisopropyl azodicarboxylate (4.5 ml, 22.9 mmol). The mixture was stirred under nitrogen atmosphere over night. The tetrahydrofuran was removed on the roto-evaporator and the remainder was taken up in methylene chloride (60 ml) and loaded onto a flash silica gel column. Elution with ethyl acetate/hexanes (19%) gave tert-butyl-2(R)-[(tert-butoxycarbonyl)amino]-3-phthalimido-propionate (3.74 g) as a white powder.

後処理

  1. customThe tetrahydrofuran was removed on the roto-evaporator
  2. washElution with ethyl acetate/hexanes (19%)

出典と根拠

ORDレコード
ord-87b689c70e5c40dd84ed6c73d448be8d
出典データセット
uspto-grants-2005_01
特許番号
US06844366B2

反応ノート

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