Dimethyl Sulfoxide → (2R)-2-(BOC)amino-N-(3-oxo-azetidine-1-yl)-3-(4-chlorophenyl)propionamide

HRID 1670030노트

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HRID 1670030 반응식
[C:1]([NH:8][C@H:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:10]([NH:12][N:13]1[CH2:16][CH:15]([OH:17])[CH2:14]1)=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(Cl)(=O)C(Cl)=O.CS(C)=O>C(Cl)Cl>[C:1]([NH:8][C@H:9]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)[C:10]([NH:12][N:13]1[CH2:14][C:15](=[O:17])[CH2:16]1)=[O:11])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 67345448(2R)-2-(BOC)Amino-N-(3-hydroxyazetidine-1-yl)-3-(4-chlorophenyl)propionamide

생성물 1

HCID 67345314(2R)-2-(BOC)amino-N-(3-oxo-azetidine-1-yl)-3-(4-chlorophenyl)propionamide수율 84%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(2R)-2-(BOC)Amino-N-(3-hydroxyazetidine-1-yl)-3-(4-chlorophenyl)propionamide (3.54 g, 10 mmol) was placed in a round-bottomed flask, filled with nitrogen, and DCM (30 mL) and oxalyl chloride (872 μl, 10 mmol) were added. The mixture was cooled to −78-C, and DMSO (709 μl, 10 mmol) was added. The reaction solution was stirred for 3 h keeping the temperature below −50° C. The reaction mixture was quenched by addition of TEA and warmed to rt. The reaction solution was diluted with a saturated aqueous NH4Cl solution, and the organic material was extracted with EtOAc. The extracts was dried over MgSO4 and concentrated in vacuo, and the residue was purified by column chomatography (eluent: EtOAc/Hex=1/3) to give the title compound (2.88 g, 84%).

후처리

  1. additionwere added
  2. additionwas added
  3. customthe temperature below −50° C
  4. customThe reaction mixture was quenched by addition of TEA
  5. additionThe reaction solution was diluted with a saturated aqueous NH4Cl solution
  6. extractionthe organic material was extracted with EtOAc
  7. dry with materialThe extracts was dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customthe residue was purified by column chomatography (eluent: EtOAc/Hex=1/3)

출처 및 근거

ORD 기록
ord-ab4d5dbf84bd4802a95abf73df053b48
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989634B2

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