tert-Butyl {4-[(2R,3R)-1-(4-fluorophenyl)-3-({[2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)-4-oxoazetidin-2-yl]phenoxy}acetate → [4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-methoxyphenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetic acid

HRID 254091Notes

Reaction equation

HRID 254091 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13][CH2:14][C:15]3([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=4)OCC(C)(C)C[O:16]3)[C@H:9]2[C:31]2[CH:45]=[CH:44][C:34]([O:35][CH2:36][C:37]([O:39]C(C)(C)C)=[O:38])=[CH:33][CH:32]=2)=[CH:4][CH:3]=1>C(O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13][CH2:14][C:15]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)=[O:16])[C@H:9]2[C:31]2[CH:45]=[CH:44][C:34]([O:35][CH2:36][C:37]([OH:39])=[O:38])=[CH:33][CH:32]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 86619090tert-Butyl {4-[(2R,3R)-1-(4-fluorophenyl)-3-({[2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)-4-oxoazetidin-2-yl]phenoxy}acetate

Product 1

HCID 66842884[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-methoxyphenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetic acidYield 89%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

tert-Butyl {4-[(2R,3R)-1-(4-fluorophenyl)-3-({[2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)-4-oxoazetidin-2-yl]phenoxy}acetate (0.65 g, 1.02 mmol) was dissolved in formic acid (10 ml) and stirred for 90 minutes. The mixture was concentrated under reduced pressure (temperature <30° C.) and the crude oil was purified by flash-chromatography (hexane:acetone:formic acid 60:40:0.1) to afford 0.45 g (88%) of the title compound as a pale yellow solid. 1H-NMR (CDCl3, 200 MHz): δ 3.9 (s, 3H), 4.1 (d, 1H), 4.1 (s, 2H), 4.7 (s, 2H), 4.9 (d, 1H), 6.9-7.1 (m, 6H), 7.2-7.4 (m, 4H), 7.9-8.0 (d, 2H). MS (CI) M/z: 494.1 (M+−1), 495.1 (M+)

Workup

  1. concentrationThe mixture was concentrated under reduced pressure (temperature <30° C.)
  2. customthe crude oil was purified by flash-chromatography (hexane:acetone:formic acid 60:40:0.1)

Sources & evidence

ORD record
ord-b93cf065754944568885e857e4654bf6
Source dataset
uspto-grants-2011_01
Patent number
US07871998B2

Reaction notes

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