1,2-Dichloroethane → HCID 69939642、化合物

HRID 1058313ノート

反応式

HRID 1058313 の反応式
C(Cl)CCl.[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:14][N:15]2[CH2:18][CH:17]([OH:19])[CH2:16]2)=[C:10]([CH:13]=1)[CH2:11][NH2:12].[C:20]([N:27]1[CH2:34][CH2:33][CH2:32][C@H:28]1[C:29](O)=[O:30])([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C1C=NC2N(O)N=NC=2C=1>CN(C=O)C>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:14][N:15]2[CH2:16][CH:17]([OH:19])[CH2:18]2)=[C:10]([CH:13]=1)[CH2:11][NH:12][C:29](=[O:30])[C@@H:28]1[CH2:32][CH2:33][CH2:34][N:27]1[C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21]

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 181649HOAtHCID 18672299HCID 18672299、化合物

生成物 1

HCID 69939642HCID 69939642、化合物収率 9.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

EDC (1.51 g, 7.87 mmol) was added to a stirred mixture of 5-chloro-2-[(3-hydroxyazetidin-1-yl)methyl]benzylamine (1.19 g, 5.25 mmol), N-Boc-L-proline (1.13 g, 5.25 mmol) and HOAT (0.36 g, 2.62 mmol) in DMF (9 mL). After 16 h the mixture was concentrated and the residue was partitioned between EtOAc and 10% NaHCO3. The organic layer was washed with water and brine, dried (Na2SO4)and evaporated. The residue was partitioned between EtOAc and 1M citric acid. The aqueous layer was made neutral with NaHCO3 and was extracted into CH2Cl2. The organic layer was evaporated and the residue was purified by chromatography on silica (ammonia saturated CHCl3/MeOH, 95:5) to give N-{5-chloro-2-[(3-hydroxyazetidin-1-yl)methyl]benzyl}-1-(tert-butoxycarbonyl)-L-prolinamide (210 mg) as a glass: MS: 424.5 (M+1).

後処理

  1. concentrationAfter 16 h the mixture was concentrated
  2. customthe residue was partitioned between EtOAc and 10% NaHCO3
  3. washThe organic layer was washed with water and brine, dried (Na2SO4)and
  4. customevaporated
  5. customThe residue was partitioned between EtOAc and 1M citric acid
  6. extractionwas extracted into CH2Cl2
  7. customThe organic layer was evaporated
  8. customthe residue was purified by chromatography on silica (ammonia saturated CHCl3/MeOH, 95:5)

出典と根拠

ORDレコード
ord-a6834300403446d6913336c75309e170
出典データセット
uspto-grants-2003_02
特許番号
US06515011B2

反応ノート

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