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Dimethyl Sulfoxide → 3-[(N-acetylprolyl)alanylprolylamino]-2,2-dihydroxybutanoic acid, methyl ester

HRID 1440060
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HRID 1440060 반응식
C(Cl)(=O)C(Cl)=[O:3].CS(C)=O.[C:11]([N:14]1[CH2:41][CH2:40][CH2:39][C@H:15]1[C:16]([NH:18][C@H:19]([C:21]([N:23]1[CH2:38][CH2:37][CH2:36][C@H:24]1[C:25]([NH:27][CH:28]([CH3:35])[CH:29]([OH:34])[C:30]([O:32][CH3:33])=[O:31])=[O:26])=[O:22])[CH3:20])=[O:17])(=[O:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[C:11]([N:14]1[CH2:41][CH2:40][CH2:39][C@H:15]1[C:16]([NH:18][C@H:19]([C:21]([N:23]1[CH2:38][CH2:37][CH2:36][C@H:24]1[C:25]([NH:27][CH:28]([CH3:35])[C:29]([OH:3])([OH:34])[C:30]([O:32][CH3:33])=[O:31])=[O:26])=[O:22])[CH3:20])=[O:17])(=[O:13])[CH3:12]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 145033163-[(N-acetylprolyl)alanylprolylamino]-2-hydroxybutanoic acid, methyl ester

생성물 1

HCID 867493313-[(N-acetylprolyl)alanylprolylamino]-2,2-dihydroxybutanoic acid, methyl ester

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
3회

실험 절차

To a stirred solution of oxalyl chloride (0.12 ml, 1.43 mmol) in methylene chloride (1.5 ml) under an argon atmosphere and cooled in a dry ice-acetone bath was added dropwise a solution of dimethylsulfoxide (0.20 ml, 2.86 mmol) in methylene chloride (1.5 ml). After 5 minutes, a solution of the product of example 59 (0.32 g, 0.72 mmol) in methylene chloride (1.5 ml) was added and the reaction mixture stirred for 25 minutes. Triethylamine (0.50 ml, 3.58 mmol) was added and the reaction mixture warmed to room temperature. The reaction mixture was placed directly onto a silica gel column and eluted with methylene chloride-methanol. Evaporation of the appropriate fractions on a rotary evaporator, addition of water (3 ml) to the residue and evaporation gave the above-namedproduct.

후처리

  1. washeluted with methylene chloride-methanol
  2. customEvaporation of the appropriate fractions
  3. customon a rotary evaporator, addition of water (3 ml)
  4. customto the residue and evaporation
  5. customgave the above-namedproduct

출처 및 근거

ORD 기록
ord-d50fac0400504deeb61de01fdaf30807
출처 데이터셋
uspto-grants-1996_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05496927

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