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Ammonium formate → HCID 10270207, 화합물

HRID 2182935
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HRID 2182935 반응식
C([O:8][NH:9][C:10](=[O:33])[CH2:11][C@H:12]([C:22]1[O:23][C:24]([CH3:32])=[C:25]([C:27]([N:29]([CH3:31])[CH3:30])=[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.[Pd]>[NH3:9].[CH:16]1([CH2:15][CH2:14][CH2:13][C@@H:12]([C:22]2[O:23][C:24]([CH3:32])=[C:25]([C:27]([N:29]([CH3:31])[CH3:30])=[O:28])[N:26]=2)[CH2:11][C:10]([NH:9][OH:8])=[O:33])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 2723923Ammonium formate2회HCID 59909793HCID 59909793, 화합물

생성물 2

HCID 222AmmoniaHCID 10270207HCID 10270207, 화합물수율 59.5%

시약·촉매·용매 2

HCID 23938Palladium촉매2회HCID 702Ethanol용매

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온도
45 °C

실험 절차

A solution of 2-((1R)-1-{2-[(benzyloxy)amino]-2-oxoethyl}-4-cyclohexylbutyl)-N,N,5-trimethyl-1,3-oxazole-4carboxamide (Preparation 73) (105 mg, 0.23 mmol) in ethanol (5 ml) was treated with 5% palladium on barium sulphate (45 mg) and ammonium formate (73 mg, 1.15 mmol) and the mixture was heated at 45° C. for 17 hours. Further palladium on barium sulphate (30 mg) and ammonium formate (60 mg, mmol) were added and the heating was continued for 2 hours. The solution was filtered through Arbocel® and the solvent removed from the filtrate under reduced pressure. The residue was azeotroped from dichloromethane (×3) then purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 ammonia (98:2:0.2 to 90:10:1) to afford the title compound as a foam (25 mg).

후처리

  1. filtrationThe solution was filtered through Arbocel®
  2. customthe solvent removed from the filtrate under reduced pressure
  3. customThe residue was azeotroped from dichloromethane (×3)
  4. customthen purified by column chromatography on silica gel eluting with dichloromethane

출처 및 근거

ORD 기록
ord-0267d917955f4695a4aa6f1faeacd870
출처 데이터셋
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06897306B2

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