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Ammonium formate → HCID 10135305, 화합물

HRID 2182952
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인쇄 미리보기

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HRID 2182952 반응식
C([O:8][NH:9][C:10](=[O:35])[CH2:11][C@H:12]([C:22]1[O:23][C:24]([CH3:34])=[C:25]([C:27]([NH:29][CH2:30][C:31]([OH:33])=[O:32])=[O:28])[N:26]=1)[CH2:13][CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[Pd+2].[OH-]>[CH:16]1([CH2:15][CH2:14][CH2:13][C@@H:12]([C:22]2[O:23][C:24]([CH3:34])=[C:25]([C:27]([NH:29][CH2:30][C:31]([OH:33])=[O:32])=[O:28])[N:26]=2)[CH2:11][C:10]([NH:9][OH:8])=[O:35])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1
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참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 59909765HCID 59909765, 화합물

생성물 1

HCID 10135305HCID 10135305, 화합물수율 35.8%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매

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온도
43 °C

실험 절차

A solution ({[2-((1R)-1-{2-[(benzyloxy)amino]-2-oxoethyl}-4-cyclohexylbutyl)-5-methyl-1,3-oxazol-4-yl]carbonyl}amino)acetic acid (Preparation 100) (60 mg, 0.12 mmol) in ethanol (3 ml) was treated with ammonium formate (78 mg, 1.23 mmol) and palladium hydroxide (20 mg) and heated at 43° C., under a nitrogen atmosphere for 4 hours. The reaction mixture was filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of 99:1:0.1 (dichloromethane:methanol:acetic acid) gradually changing to 90:10:1 (dichloromethane:methanol:acetic acid) to afford the title compound as a white solid (17 mg).

후처리

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent removed under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of 99:1:0.1 (dichloromethane:methanol:acetic acid)

출처 및 근거

ORD 기록
ord-659f709e5acf454c86b15d4983af8268
출처 데이터셋
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06897306B2

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