Water → tert-butyl {2-[(1S,2R)-1,2-dihydroxypropyl]benzyl}carbamate

HRID 923483노트

반응식

HRID 923483 반응식
CS(N)(=O)=O.[OH2:6].[CH:7](/[C:10]1[CH:24]=[CH:23][CH:22]=[CH:21][C:11]=1[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:8]/[CH3:9].S([O-])([O-])(=[O:27])=S.[Na+].[Na+]>C(O)(C)(C)C>[OH:6][C@@H:7]([C:10]1[CH:24]=[CH:23][CH:22]=[CH:21][C:11]=1[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:19])[CH3:17])[C@H:8]([OH:27])[CH3:9]

참가 물질

6

반응물 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 72879MethanesulfonamideHCID 118318066tert-butyl {2-[(1Z)-prop-1-en-1-yl]benzyl}carbamate

생성물 1

HCID 118318079tert-butyl {2-[(1S,2R)-1,2-dihydroxypropyl]benzyl}carbamate

시약·촉매·용매 1

HCID 6386tert-Butanol용매2회

실험 절차

To a mixture of 3.30 g of AD mix-α, 200 mg of methanesulfonamide, 12.5 ml of tert-butyl alcohol, and 12.5 ml of water was added a solution of 500 mg of tert-butyl {2-[(1Z)-prop-1-en-1-yl]benzyl}carbamate in 5 ml of tert-butyl alcohol, followed by stirring at room temperature for 12 hours. To the reaction mixture was added sodium thiosulfate, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 449 mg of tert-butyl {2-[(1S,2R)-1,2-dihydroxypropyl]benzyl}carbamate.

후처리

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was then evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-195099e262304b24bca2d9c68b8c5fec
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278968B2

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