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

HRID 254113Notes

Reaction equation

HRID 254113 reaction equation
[Cl: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]([Cl:29])=[CH:25][CH:24]=4)OCC(C)(C)C[O:16]3)[C@H:9]2[C:30]2[CH:44]=[CH:43][C:33]([O:34][CH2:35][C:36]([O:38]C(C)(C)C)=[O:37])=[CH:32][CH:31]=2)=[CH:4][CH:3]=1>C(O)=O>[Cl: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:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=3)=[O:16])[C@H:9]2[C:30]2[CH:44]=[CH:43][C:33]([O:34][CH2:35][C:36]([OH:38])=[O:37])=[CH:32][CH:31]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 86619095tert-Butyl {4-[(2R,3R)-1-(4-chlorophenyl)-3-({[2-(4-chlorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)-4-oxoazetidin-2-yl]phenoxy}acetate

Product 1

HCID 66842820[4-((2R,3R)-1-(4-Chlorophenyl)-3-{[2-(4-chlorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetic acidYield 81.4%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

tert-Butyl {4-[(2R,3R)-1-(4-chlorophenyl)-3-({[2-(4-chlorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)-4-oxoazetidin-2-yl]phenoxy}acetate (1.69 g, 2.57 mmol) was dissolved in formic acid (25 ml) and stirred for two hours. 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 1.08 g (81%) of the title compound as a pale yellow solid. 1H-NMR (CDCl3, 200 MHz): δ 4.0-4.2 (m, 3H), 4.7 (s, 2H), 4.9 (d, 1H), 6.9 (d, 2H), 7.2-7.4 (m, 6H), 7.5 (d, 2H), 7.9 (d, 2H). MS (CI) M/z: 514.2 (NT), 515.2 (30), 516.1 (70), 517.2 (20).

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-d937cbf4ebf3410a9775c20029be9da9
Source dataset
uspto-grants-2011_01
Patent number
US07871998B2

Reaction notes

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