Acetic Acid → HCID 57654653, 화합물

HRID 1175128노트

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HRID 1175128 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 57654653HCID 57654653, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

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온도
-5 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-6434a0738b8845ea8228d4f9ffac7488
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838674B2

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