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

HRID 603918Notes

Reaction equation

HRID 603918 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH2:18][S:19][C@H:20]4[C:23](=[O:24])[N:22]([C:25]5[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=5)[C@@H:21]4[C:32]4[CH:46]=[CH:45][C:35]([O:36][CH2:37][C:38]([O:40]C(C)(C)C)=[O:39])=[CH:34][CH:33]=4)OCC(C)(C)C[O:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1>C(O)=O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:11])[CH2:18][S:19][C@H:20]3[C:23](=[O:24])[N:22]([C:25]4[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=4)[C@@H:21]3[C:32]3[CH:33]=[CH:34][C:35]([O:36][CH2:37][C:38]([OH:40])=[O:39])=[CH:45][CH:46]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

3

Reactant 1

HCID 86643075tert-Butyl {4-[(2R,3R)-3-({[2-(1,3-benzodioxol-5-yl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetate

Product 1

HCID 67271538{4-[(2R,3R)-3-{[2-(1,3-benzodioxol-5-yl)-2-oxoethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetic acid

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

tert-Butyl {4-[(2R,3R)-3-({[2-(1,3-benzodioxol-5-yl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetate (Method 16) (10.0 g, 15.35 mmol) was dissolved in formic acid (100 mL) at room temperature and stirred for two hours. The mixture was concentrated under reduced pressure (temperature<30° C.) and the crude oil was purified by flash-chromatography (heptane:acetone:formic acid 6:4:0.01 and then 5:5:0.01) to afford the title compound.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure (temperature<30° C.)
  2. customthe crude oil was purified by flash-chromatography (heptane:acetone:formic acid 6:4:0.01

Sources & evidence

ORD record
ord-187aaa2583234c1f8650f3b05b967b86
Source dataset
uspto-grants-2011_03
Patent number
US07906502B2

Reaction notes

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