Dimethylformamide → BOC-Cys(Acm)-Asp(OBzl)-OH

HRID 435407

반응식

HRID 435407 반응식
[NH:1]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@H:2]([C:10]([O:12]N1C(=O)CCC1=O)=O)[CH2:3][S:4][CH2:5][NH:6][C:7]([CH3:9])=[O:8].[NH2:27][C@H:28]([C:40]([OH:42])=[O:41])[CH2:29][C:30](=[O:39])[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.CN1CCOCC1.CN(C=O)C>C1COCC1>[NH:1]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[C@H:2]([C:10]([NH:27][C@H:28]([C:40]([OH:42])=[O:41])[CH2:29][C:30](=[O:39])[O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:12])[CH2:3][S:4][CH2:5][NH:6][C:7]([CH3:9])=[O:8]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 1011864-(Phenylmethyl) hydrogen L-aspartateHCID 14258357HCID 14258357, 화합물

생성물 1

HCID 131713062BOC-Cys(Acm)-Asp(OBzl)-OH수율 62.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

BOC-Cys(Acm)-OSu (77.5 g, 198 mM) was dissolved in THF (400 ml). H-Asp(OBzl)-OH (44.64 g, 200 mM) was added thereto, and the mixture was adjusted to pH 7 by adding NMM (18 ml) at 0° C.; DMF (300 ml) was added and the mixture was stirred overnight. The DMF was removed in vacuo, and 5% sodium bicarbonate (150 ml) was added to the residue, which was then washed twice with ether. The aqueous layer was adjusted to pH 3 by adding 1 N HCl (200 ml) to precipitate an oily material, which was extracted three times with ethyl acetate (300 ml), and the ethyl acetate layer was washed three times with aqueous sodium chloride and water. After drying with anhydrous sodium sulfate, the solution was concentrated in vacuo. Ether and hexane were added to the residue to obtain a precipitate. Recrystallization was effected with ethyl acetate-ether to yield the substance [42] (61.98 g, yield: 62.9%).

후처리

  1. customThe DMF was removed in vacuo, and 5% sodium bicarbonate (150 ml)
  2. additionwas added to the residue, which
  3. washwas then washed twice with ether
  4. additionby adding 1 N HCl (200 ml)
  5. customto precipitate an oily material, which
  6. extractionwas extracted three times with ethyl acetate (300 ml)
  7. washthe ethyl acetate layer was washed three times with aqueous sodium chloride and water
  8. dry with materialAfter drying with anhydrous sodium sulfate
  9. concentrationthe solution was concentrated in vacuo
  10. additionEther and hexane were added to the residue
  11. customto obtain a precipitate
  12. customRecrystallization

출처 및 근거

ORD 기록
ord-f288ba8dd6db4f58a2e9c91c5a6ab292
출처 데이터셋
uspto-grants-1983_08
특허 번호
US04400316

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