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 425802ノート

反応式

HRID 425802 の反応式
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

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-411e7770552146b6a202d07c7912e894
出典データセット
uspto-grants-2012_01
特許番号
US08106215B2

反応ノート

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