Water → Fmoc-(RS)-3-amino-3-(4-nitrophenyl)-propionic acid

HRID 967010

반응식

HRID 967010 반응식
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].[CH:16]1[C:28]2[CH:27]([CH2:29][O:30][C:31](C3CC(=O)N(O)C3=O)=[O:32])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1.O>C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>[CH:16]1[C:28]2[CH:27]([CH2:29][O:30][C:31]([NH:1][CH:2]([C:7]3[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=3)[CH2:3][C:4]([OH:6])=[O:5])=[O:32])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 37962843-amino-3-(4-nitrophenyl)propanoic AcidHCID 21653429Fmoc-N-hydroxysuccinimide

생성물 1

HCID 2759202Fmoc-(RS)-3-amino-3-(4-nitrophenyl)-propionic acid수율 43.6%

시약·촉매·용매 2

HCID 10340Sodium Carbonate용매HCID 312751,4-Dioxane용매2회

실험 절차

A cold (0°) solution of 3-amino-3-(4-nitrophenyl)propanoic acid (3.2 g, 15 mmol) in 10% aqueous sodium carbonate (60 ml) and 1,4-dioxan (30 ml) was treated portion-wise with 9-fluorenylmethoxycarbonyl-N-hydroxysuccinimide (5.6 g, 17 mmol) in 1,4-dioxan (15 ml) and the mixture stirred at room temperature for 12 h. The mixture was poured into water (300 ml) and the aqueous phase washed 3 times with ether. The aqueous layer was then acidified with solid citric acid and extracted into ether. The combined organic layers were dried (MgSO4) and evaporated to a yellow oil then triturated from hexane and EtOAc to afford the title compound as a yellow solid (2.83 g); m/z (ES+, 70V) 432 (MH+).

후처리

  1. washthe aqueous phase washed 3 times with ether
  2. extractionextracted into ether
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. customevaporated to a yellow oil
  5. customthen triturated from hexane and EtOAc

출처 및 근거

ORD 기록
ord-2d6f115e020045ba9cc54f5936f68b3c
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06953798B1

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