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4-Methylmorpholine → (2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-(3-(4-nitrobenzyloxycarbonylmethylaminocarbonyl)phenylcarbamoyl)-pyrrolidine

HRID 260314
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HRID 260314 반응식
[C:1]([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C@H:7]([C:23](=[O:34])[NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([OH:33])=O)[CH:26]=2)[CH2:6]1)(=[O:3])[CH3:2].C(Cl)(=O)C(Cl)=O.Cl.[NH2:42][CH2:43][C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][C:51]([N+:54]([O-:56])=[O:55])=[CH:50][CH:49]=1)=[O:45].CN1CCOCC1>ClCCl.CN(C)C=O>[C:1]([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=2)=[O:11])[C@H:7]([C:23](=[O:34])[NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([NH:42][CH2:43][C:44]([O:46][CH2:47][C:48]3[CH:53]=[CH:52][C:51]([N+:54]([O-:56])=[O:55])=[CH:50][CH:49]=3)=[O:45])=[O:33])[CH:26]=2)[CH2:6]1)(=[O:3])[CH3:2]
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참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 65578Oxalyl chloride2회HCID 22401149Glycine p-nitrobenzyl ester hydrochlorideHCID 57213936(2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-(3-carboxyphenylcarbamoyl)pyrrolidine

생성물 1

HCID 57286643(2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-(3-(4-nitrobenzyloxycarbonylmethylaminocarbonyl)phenylcarbamoyl)-pyrrolidine
수율 55.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매2회HCID 6344Dichloromethane용매4회

실험 절차

To a solution of (2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-(3-carboxyphenylcarbamoyl)pyrrolidine (0.49 g, 1 mM) in dichloromethane (10 ml) was added oxalyl chloride (0.20 ml. 1.1 mM) and dimethylformamide (2-3 drops). After 1 hour a further amount of oxalyl chloride (0.20 ml, 1.1 mM) and DMF (2-3 drops) were added and the mixture stirred for a further hour. The solution was evaporated to leave a yellow gum. The gum was dissolved in dichloromethane (10 ml) and added to a suspension of 4-nitrobenzyl 2-aminoethanoate hydrochloride salt (0.30 g, 1.2 mM) and N-methylmorpholine (0.27 ml, 2.4 mM) in dichloromethane (10 ml). After 17 hours the mixture was diluted with dichloromethane (80 ml), washed with water (20 ml), brine (20 ml) and dried (MgSO4). Purification by flash chromatography through silica using a gradient of dichloromethane to ethyl acetate as eluent gave (2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-(3-(4-nitrobenzyloxycarbonylmethylaminocarbonyl)phenylcarbamoyl)-pyrrolidine (380 mg).

후처리

  1. customThe solution was evaporated
  2. customto leave a yellow gum
  3. washwashed with water (20 ml), brine (20 ml)
  4. dry with materialdried (MgSO4)
  5. customPurification by flash chromatography through silica using a gradient of dichloromethane to ethyl acetate as eluent

출처 및 근거

ORD 기록
ord-65144a5d56fa4bf49870ae86bbac6abd
출처 데이터셋
uspto-grants-1996_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05527791

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