Triethylamine → (2S,3R)-3-Allyl-4-oxo-1-(1-phenyl-propylcarbamoyl)-azetidine-2-carboxylic acid 4-methoxy-benzyl ester

HRID 1783427ノート

反応式

HRID 1783427 の反応式
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]([C@@H:11]2[C@@H:14]([CH2:15][CH:16]=[CH2:17])[C:13](=[O:18])[NH:12]2)=[O:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH2:28]([CH:30]([N:37]=[C:38]=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:29]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([C@@H:11]2[C@@H:14]([CH2:15][CH:16]=[CH2:17])[C:13](=[O:18])[N:12]2[C:38](=[O:39])[NH:37][CH:30]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:28][CH3:29])=[O:10])=[CH:19][CH:20]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 15563476(1-Isocyanatopropyl)benzeneHCID 57589773(2S,3R)-3-Allyl-4-oxo-azetidine-2-carboxylic acid 4-methoxy-benzyl ester

生成物 1

HCID 68603869(2S,3R)-3-Allyl-4-oxo-1-(1-phenyl-propylcarbamoyl)-azetidine-2-carboxylic acid 4-methoxy-benzyl ester収率 59%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of compound 59 (41 mg, 0.15 mmol), triethylamine (83 uL, 0.60 mmol), α-ethyl-benzyl isocyanate (29 mg, 0.18 mmol) in methylene chloride (1.2 mL) was stirred overnight. TLC analysis indicated the completion the reaction. Removal of solvents gave the crude material, which was purified by preparative TLC plate (15% EtOAc in hexanes), yielding 38.2 mg of compound 60 (59%): LC-MS purity: 98.1%; 1HNMR (300 MHz, CDCl3): 0.95 (t, 3H), 1.92 (m, 2H), 2.69 (m, 2H), 3.30 (m, 1H), 3.83 (s, 3H), 4.22 (d, 1H), 4.85 (q, 1H), 5.18 (m, 4H), 5.80 (m, 1H), 6.85 (br, d, 1H), 7.45 (m, 9H). Anal. C25H28N2O5, Mol. Wt.: 436.5. Found: ESI-MS: 437.1 (M+H)+.

後処理

  1. customthe reaction
  2. customRemoval of solvents
  3. customgave the crude material, which
  4. customwas purified by preparative TLC plate (15% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-5f9ae00d60e145d8aec04edc69a01edb
出典データセット
uspto-grants-2009_03
特許番号
US07501404B2

反応ノート

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