Diethyl Ether → [(1S,2S,5R)-2-aminomethyl-7-methyl-3-aza-bicyclo[3.3.0]oct-3-yl]-(2-methyl-5-m-tolyl-thiazol-4-yl)-methanone

HRID 425802노트

반응식

HRID 425802 반응식
FC(F)(F)C([NH:5][CH2:6][C@H:7]1[N:14]([C:15]([C:17]2[N:18]=[C:19]([CH3:29])[S:20][C:21]=2[C:22]2[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=2)=[O:16])[CH2:13][C@H:12]2[C@@H:8]1[CH2:9][CH:10]([CH3:30])[CH2:11]2)=O.C([O-])([O-])=O.[K+].[K+].CCOCC>CO>[NH2:5][CH2:6][C@H:7]1[N:14]([C:15]([C:17]2[N:18]=[C:19]([CH3:29])[S:20][C:21]=2[C:22]2[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=2)=[O:16])[CH2:13][C@H:12]2[C@@H:8]1[CH2:9][CH:10]([CH3:30])[CH2:11]2

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 866435452,2,2-trifluoro-N-[(1S,2S,5R)-3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-7-methyl-3-aza-bicyclo[3.3.0]oct-2-ylmethyl]-acetamide

생성물 1

HCID 59411601[(1S,2S,5R)-2-aminomethyl-7-methyl-3-aza-bicyclo[3.3.0]oct-3-yl]-(2-methyl-5-m-tolyl-thiazol-4-yl)-methanone

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

2,2,2-trifluoro-N-[(1S,2S,5R)-3-(2-methyl-5-m-tolyl-thiazole-4-carbonyl)-7-methyl-3-aza-bicyclo[3.3.0]oct-2-ylmethyl]-acetamide (1.96 g) was dissolved in MeOH (20 mL) and a sat. aq. K2CO3 solution was added (20 mL). The reaction mixture was stirred overnight at RT. Ether was added to the reaction mixture and the org. layer was extracted with aq. HCl (25%) and aq. HCl (1M). The org. phase was discarded and the aq. layers were basified with aq. 30% NaOH and then extracted with DCM. The combined org. extracts were washed with a sat. aq. NaHCO3 solution, dried over anh. MgSO4, filtered and concentrated to yield the title compound as a light orange oil which was used without further purification.

후처리

  1. extractionlayer was extracted with aq. HCl (25%) and aq. HCl (1M)
  2. extractionextracted with DCM
  3. washextracts were washed with a sat. aq. NaHCO3 solution
  4. dry with materialdried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-411e7770552146b6a202d07c7912e894
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106215B2

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