Acetic Acid → HCID 57654653、化合物

HRID 1175128ノート

反応式

HRID 1175128 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([CH2:12][OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31].C(O)(=O)C>C(Cl)Cl.O>[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([CH2:12][O:13][S:30]([CH3:29])(=[O:32])=[O:31])[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 576546571,1-Dimethylethyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-3-(hydroxymethyl)-1-azetidinecarboxylate

生成物 1

HCID 57654653HCID 57654653、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
-5 °C

実験手順

3-tert-Butoxycarbonylamino-3-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester (490 mg; 1.6 mmol) and triethylamine (1.7 ml; 19 mmol), dissolved in CH2Cl2 (3 ml), are cooled to −5° C. and treated with methanesulfonyl chloride (280 mg; 2.43 mmol). The reaction mixture is kept at 0° C. for 35 minutes, poured on 10% acetic acid in water and extracted with TBME. The combined organic phases are washed with 2N Na2CO3, dried over Na2SO4, filtered and evaporated to dryness, yielding the desired product as colorless crystals. 1H-NMR (400 MHz; DMSO-d6: 7.75 (bs, 1H); 4.40 (s, 2H); 3.81 (bs, 4H); 3.23 (s, 3H); 1.40 (s, 9H); 1.38 (s, 9H). MS (m/z) ES+: 381 (MH+).

後処理

  1. extractionextracted with TBME
  2. washThe combined organic phases are washed with 2N Na2CO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-6434a0738b8845ea8228d4f9ffac7488
出典データセット
uspto-grants-2010_11
特許番号
US07838674B2

反応ノート

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