Methanol → (1-{1-[4-Benzylcarbamoyl-6-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl ester

HRID 1965192ノート

反応式

HRID 1965192 の反応式
[CH2:1]([O:8][C:9](=[O:41])[N:10]([CH:12]([C:14](=[O:40])[NH:15][CH:16]([C:21]([N:23]1[CH2:27][CH2:26][CH:25]2[NH:28][CH2:29][CH:30]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)[CH:24]12)=[O:22])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:42]([N:49]=[C:50]=[O:51])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.CO.[NH4+].[OH-]>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:41])[N:10]([CH:12]([C:14](=[O:40])[NH:15][CH:16]([C:21]([N:23]1[CH2:27][CH2:26][CH:25]2[N:28]([C:50](=[O:51])[NH:49][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH2:29][CH:30]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)[CH:24]12)=[O:22])[C:17]([CH3:19])([CH3:18])[CH3:20])[CH3:13])[CH3:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 76639Benzyl isocyanateHCID 67609530HCID 67609530、化合物

生成物 1

HCID 67609238(1-{1-[4-Benzylcarbamoyl-6-(4-fluoro-benzyloxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl ester収率 121%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Bicyclic amine 49 (300 mg, 0.53 mmol) and TEA (150 μL) were dissolved in DCM (5 mL) at ambient temperature and benzyl isocyanate (135 μL, 1.06 mmol) was added. After 3 h, MeOH (20 mL) and 30% NH4OH (1 mL) were added and the solution was stirred for 15 min before being concentrated in vacuo. The residue was dissolved in EtOAc and washed successively with 1N HCl, water, aqueous NaHCO3, water, and brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to afford 450 mg of 50 as an amorphous solid which was used without further purification. Mass spectrum, m/z [702.3] (M+Na)+.

後処理

  1. concentrationbefore being concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed successively with 1N HCl, water, aqueous NaHCO3, water, and brine
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-a5088faf573545ccb4d51e8c3be22b6e
出典データセット
uspto-grants-2013_04
特許番号
US08415486B2

反応ノート

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