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4-Hydroxybenzoic Acid → 4-Hydroxybenzoyl-(2S)-2-benzyloxycarbonylamino-beta-alanine tert-butyl ester

HRID 612854
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인쇄 미리보기

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HRID 612854 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[NH2:11][CH2:12][C@H:13]([NH:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[C:17]([O:16][C:14](=[O:15])[C@@H:13]([NH:21][C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])[CH2:12][NH:11][C:6](=[O:8])[C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:10][CH:9]=1)([CH3:20])([CH3:18])[CH3:19]
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참가 물질

6

반응물 4

HCID 1354-Hydroxybenzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 10803731(S)-tert-Butyl 3-amino-2-(((benzyloxy)carbonyl)amino)propanoate

생성물 1

HCID 153806404-Hydroxybenzoyl-(2S)-2-benzyloxycarbonylamino-beta-alanine tert-butyl ester

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
0 °C

실험 절차

1.41 g (10.2 mmol) of 4-hydroxybenzoic acid and 3 g (10.2 mmol) of (1.1) were suspended in 25 ml of DMF. 1.38 g (10.2 mmol) of 1-hydroxy-benzotriazole (HOBt) and, at 0° C., dicyclohexylcarbodiimide (DCCI) were added. The mixture was stirred at 0° C. for 1 h and allowed to stand at room temperature overnight. After filtration, the solvent was removed in vacuo and the residue was chromatographed on silica gel by means of MPLC using heptanelethyl acetate (1/1). (1.2) was obtained as a colorless solid; melting point 69° C.

후처리

  1. waitto stand at room temperature overnight
  2. filtrationAfter filtration
  3. customthe solvent was removed in vacuo
  4. customthe residue was chromatographed on silica gel by means of MPLC

출처 및 근거

ORD 기록
ord-86436cf819b44b73973f891ebe26eac8
출처 데이터셋
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06005117

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