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 603911Notes

Reaction equation

HRID 603911 reaction equation
[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

Participants

4

Reactant 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

Product 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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9869aeb641ab426582d68b8833948da9
Source dataset
uspto-grants-2011_03
Patent number
US07906502B2

Reaction notes

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