Morpholine → 2(R)-benzyloxycarbonylamino-3-(morpholin-4-sulfonyl)propionic acid benzyl ester

HRID 1696058노트

반응식

HRID 1696058 반응식
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[CH2:16]([O:23][C:24](=[O:42])[CH:25]([NH:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[CH2:26][S:27](Cl)(=[O:29])=[O:28])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(#N)C.C(Cl)Cl>[CH2:16]([O:23][C:24](=[O:42])[C@@H:25]([NH:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[CH2:26][S:27]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)(=[O:29])=[O:28])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

참가 물질

6

반응물 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 866343682-Benzyloxycarbonylamino-3-chlorosulfonylpropionic acid benzyl ester

생성물 1

HCID 672778622(R)-benzyloxycarbonylamino-3-(morpholin-4-sulfonyl)propionic acid benzyl ester수율 99.2%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

To a solution of morpholine (Aldrich, 1.27 mL, 14.6 mmol) and N,N-diisopropyl-N-ethylamine (DIPEA, Aldrich, 2.5 mL, 14.6 mmol) in acetonitrile (25 mL) at rt is added solid 2-benzyloxycarbonylamino-3-chlorosulfonylpropionic acid benzyl ester (3.0 g, 7.3 mmol), (prepared as described in Ross, D. L.; Skinner, C. G.; Shive, W. J. Org. Chem. 1959, 24, 1372-1374; and b) Byrnes, S.; Burckart, G. J.; Mokotoff, M. J. Med. Chem. 1978, 21, 45-49], in small portions over 10 min. A clear colorless solution resulted from which white solid began to precipitate within minutes. After 10 min, a thick white suspension was formed. The reaction was diluted in CH2Cl2 to redissolve all solids and the solution washed with 1M HCl. The aqueous layer was separated and extracted with additional CH2Cl2. The organic layer was washed with brine and dried over anhydrous Na2SO4. Following concentration in vacuo, 3.35 g (99%) of 2(R)-benzyloxycarbonylamino-3-(morpholin-4-sulfonyl)propionic acid benzyl ester was obtained as a white solid.

후처리

  1. customA clear colorless solution resulted from which white solid
  2. customto precipitate within minutes
  3. waitAfter 10 min
  4. customa thick white suspension was formed
  5. dissolutionto redissolve all solids
  6. washthe solution washed with 1M HCl
  7. customThe aqueous layer was separated
  8. extractionextracted with additional CH2Cl2
  9. washThe organic layer was washed with brine
  10. dry with materialdried over anhydrous Na2SO4
  11. concentrationconcentration in vacuo

출처 및 근거

ORD 기록
ord-eb3a472a4c4b435cb2c13994e4415a4b
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163735B2

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