Methanol → {4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetic acid

HRID 603911ノート

反応式

HRID 603911 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([OH:49])[CH2:11][S:12][C@H:13]3[C:16](=[O:17])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[C@@H:14]3[C:25]3[CH:48]=[CH:47][C:28]([O:29][CH2:30][C:31](NCC(N[C@@H](C(O)=O)CCCCN)=O)=[O:32])=[CH:27][CH:26]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[BH4-].[Na+].C[OH:53]>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([OH:49])[CH2:11][S:12][C@H:13]3[C:16](=[O:17])[N:15]([C:18]4[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=4)[C@@H:14]3[C:25]3[CH:48]=[CH:47][C:28]([O:29][CH2:30][C:31]([OH:32])=[O:53])=[CH:27][CH:26]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

参加物

4

反応物 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 67271513N-({4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-D-lysine

生成物 1

HCID 67270855{4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetic acid

実験手順

To a solution of {4-[(2R,3R)-3-{[2-(1,3-Benzodioxol-5-yl)-2-oxoethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetic acid (Method 7) (0.010 g, 0.020 mmol) in methanol (2 ml) was added NaBH4 (0.010 g, 0.265 mmol). After 15 min the reaction was quenched by the addition of an aqueous solution of hydrochloric acid (1M, 1 ml) and most of the methanol was removed under reduced pressure. The remaining solution was purified by preparative HPLC using a gradient of 20-60% MeCN in a 0.1M ammonium acetate buffer as eluent. Freeze-drying of the pure fractions gave the product.

後処理

  1. customAfter 15 min the reaction was quenched by the addition of an aqueous solution of hydrochloric acid (1M, 1 ml) and most of the methanol
  2. customwas removed under reduced pressure
  3. customThe remaining solution was purified by preparative HPLC
  4. customFreeze-drying of the pure fractions
  5. customgave the product

出典と根拠

ORDレコード
ord-9869aeb641ab426582d68b8833948da9
出典データセット
uspto-grants-2011_03
特許番号
US07906502B2

反応ノート

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