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 464568ノート

反応式

HRID 464568 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9735c05e00f94508a776e368e5866ff3
出典データセット
uspto-grants-1985_10
特許番号
US04548751

反応ノート

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