Potassium Carbonate → (3S-trans)-2-[[3-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-methyl-2-oxo-1-azetidinyl]oxy]-3-(phenylmethoxy)propanoic acid, diphenylmethyl ester

HRID 464568노트

반응식

HRID 464568 반응식
[CH3:1][C:2]([CH3:15])([O:4][C:5]([NH:7][C@H:8]1[C@H:11]([CH3:12])[N:10]([OH:13])[C:9]1=[O:14])=[O:6])[CH3:3].Br[C@@H:17]([CH2:34][O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:18]([O:20][CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:15][C:2]([CH3:1])([O:4][C:5]([NH:7][C@H:8]1[C@H:11]([CH3:12])[N:10]([O:13][CH:17]([CH2:34][O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:18]([O:20][CH:21]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[C:9]1=[O:14])=[O:6])[CH3:3]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 12946603tert-butyl N-[(2S,3S)-1-hydroxy-2-methyl-4-oxoazetidin-3-yl]carbamateHCID 13505683(S)-2-Bromo-3-(phenylmethoxy)propanoic acid, diphenylmethyl ester

생성물 1

HCID 86740377(3S-trans)-2-[[3-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-methyl-2-oxo-1-azetidinyl]oxy]-3-(phenylmethoxy)propanoic acid, diphenylmethyl ester수율 74.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (3S-trans)-[[(1,1-dimethylethoxy)carbonyl]amino]-4-methyl-1-hydroxy-2azetidinone (55 mg, 0.26 mmol) and (S)-2-bromo-3-(phenylmethoxy)propanoic acid, diphenylmethyl ester (110 mg, 0.26 mmol) in dimethylformamide (1 ml) was added potassium carbonate (100 mg, 1 mmol). The resulting slurry was stirred for three hours at room temperature, quenched with hydrochloric acid (1N, 10 ml) and extracted with ether (20 ml). The organic layer was washed twice with dilute hydrochloric acid (1N, 2×10 ml), with saturated sodium chloride solution (20 ml), dried over magnesium sulfate and evaporated at reduced pressure. Purification of the product by preparative thin layer chromatography afforded the title compound (108 mg) as a mixture of diastereomers.

후처리

  1. customquenched with hydrochloric acid (1N, 10 ml)
  2. extractionextracted with ether (20 ml)
  3. washThe organic layer was washed twice with dilute hydrochloric acid (1N, 2×10 ml), with saturated sodium chloride solution (20 ml)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated at reduced pressure
  6. customPurification of the product by preparative thin layer chromatography

출처 및 근거

ORD 기록
ord-9735c05e00f94508a776e368e5866ff3
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04548751

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