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Dimethyl Sulfoxide → Benzyl [2-(2-oxobutylcarbamoyl)ethyl]carbamate

HRID 1804553
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HRID 1804553 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([CH2:30][CH3:31])[CH2:13][NH:14][C:15]([CH2:17][CH2:18][NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:16].C(N(CC)CC)C>ClCCl>[O:11]=[C:12]([CH2:30][CH3:31])[CH2:13][NH:14][C:15]([CH2:17][CH2:18][NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:16]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

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6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 57637120Benzyl [2-(2-hydroxybutylcarbamoyl)ethyl]carbamate

생성물 1

HCID 57637089Benzyl [2-(2-oxobutylcarbamoyl)ethyl]carbamate

시약·촉매·용매 1

HCID 6344Dichloromethane용매4회

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온도
-53 °C

실험 절차

2.20 ml (26.05 mmol) oxalyl chloride are placed in 10 ml dichloromethane, the solution is cooled to −53° C. 2.45 ml (34.49 mmol) dimethylsulphoxide in 5 ml dichloromethane are slowly added dropwise, the mixture is stirred for 0.25 hours, then a solution of 6.30 g (21.40 mmol) benzyl [2-(2-hydroxy-butylcarbamoyl)-ethyl]-carbamate in 30 ml dichloromethane is added. The mixture is stirred for 1.5 hours at −60° C., then 12.60 ml triethylamine are added dropwise. The suspension is stirred for 1 hour at −50° C., then within 16 hours allowed to come up to ambient temperature. The reaction mixture is diluted with dichloromethane and extracted with 1 molar hydrochloric acid, 1 molar sodium carbonate solution and water. The organic phase is dried and evaporated to dryness.

후처리

  1. stirringThe mixture is stirred for 1.5 hours at −60° C.
  2. stirringThe suspension is stirred for 1 hour at −50° C.
  3. waitwithin 16 hours allowed
  4. customto come up to ambient temperature
  5. extractionextracted with 1 molar hydrochloric acid, 1 molar sodium carbonate solution and water
  6. customThe organic phase is dried
  7. customevaporated to dryness

출처 및 근거

ORD 기록
ord-256f8cb1b192436d987cb21013c8e73b
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08354418B2

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