Penicillin G → 4-methoxybenzyl (2RS)-2-hydroxy-2-[(3R,4R)-4-mercapto-3-phenylacetamidoazetidin-2-on-1-yl]acetate

HRID 612283

反応式

HRID 612283 の反応式
C1(C)C=CC(S(O)(=O)=[O:8])=CC=1.[OH:12][CH:13]([N:26]1[C:32](=[O:33])[C@@H:31]2[C@H:27]1[S:28][C:29]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[N:30]2)[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)=[O:15].CC1(C)S[C@@H]2[C@H](NC(CC3C=CC=CC=3)=O)C(=O)N2[C@H]1C(O)=O.CC1(C)S[C@@H]2[C@H](NC(COC3C=CC=CC=3)=O)C(=O)N2[C@H]1C(O)=O>O.ClCCl.CC(C)=O>[OH:12][CH:13]([N:26]1[C@H:27]([SH:28])[C@H:31]([NH:30][C:29](=[O:8])[CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:32]1=[O:33])[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)=[O:15]

参加物

8

反応物 4

HCID 5904Penicillin GHCID 6101p-Toluenesulfonic acidHCID 6869Penicillin VHCID 536561234-Methoxybenzyl (RS)-2-hydroxy-2-[(lR,5R)-3-benzyl-4-thia-2,6-diazabicyclo[3.2.0)hept-2-en-7-on-6-yl]acetate

生成物 1

HCID 544549564-methoxybenzyl (2RS)-2-hydroxy-2-[(3R,4R)-4-mercapto-3-phenylacetamidoazetidin-2-on-1-yl]acetate

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

Toluene-4-sulphonic acid (6.0 g, 31.5 mmol) in water (15 ml) was added to a solution of 4-methoxybenzyl (2RS)-2-hydroxy-2-[(1R,5R)-3-benzyl-4-thia-2,6-diazabicyclo [3.2.0]hept-2-en-7-on-6-yl]acetate (7.42 g, 18.0 mmol) prepared from Penicillin G as described for the benzhydryl ester derived from Penicillin V, S. Yamamoto, N. Haga, T. Aoki, S. Hayashi, H. Tanida, and W. Nagata, Heterocycles, 1977, 8, 283) in dichloromethane (30 ml) and acetone (30 ml). After stirring for 2.5 h at room temperature, the reaction mixture was diluted with dichloromethane, washed with water (x2), dried and concentrated in vacuo to yield crude 4-methoxybenzyl (2RS)-2-hydroxy-2-[(3R, 4R) -4-mercapto-3-phenylacetamidoazetidin-2-on-1-yl]acetate as a yellow foam.

後処理

  1. washwashed with water (x2)
  2. customdried
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-1901329767fd44ac8a585b20528d782e
出典データセット
uspto-grants-1999_12
特許番号
US06001997

関連ノート

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