Benzoic Acid → HCID 131721506, compound

HRID 376586Notes

Reaction equation

HRID 376586 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[O:8][CH:7]([C:9]([CH2:11][S:12][C@H:13]2[N:16]([C:17](=P(CCCC)(CCCC)CCCC)[C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)=[O:19])[C:15](=[O:43])[C@H:14]2[NH:44][C:45](=[O:54])[CH2:46][O:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=O)[CH2:6][CH2:5]1.C(O)(=O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][CH:4]1[O:8][CH:7]([C:9]2[CH2:11][S:12][C@@H:13]3[C@H:14]([NH:44][C:45](=[O:54])[CH2:46][O:47][C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=4)[C:15](=[O:43])[N:16]3[C:17]=2[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[O:19])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 243Benzoic AcidHCID 88237107HCID 88237107, compound

Product 1

HCID 131721506HCID 131721506, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-methoxybenzyl 2-[(3R,4R)-4-[(2RS,5SR)-5-methoxymethyltetrahydrofuran-2-ylcarbonylmethylthio]-3-phenoxyacetamidoazetidin-2-on-1-yl]-2-tri-n-butylphosphoranylideneacetate (4.25g) and benzoic acid (20mg) in toluene (100ml) was heated to reflux for 10h. The mixture was cooled and the solvent evaporated. The product (1.93g) was isolated by column chromatography of the residue using gradient elution (silica gel 1:1 hexane : ethyl acetate going to neat ethyl acetate); vmax (CHCl3) 3409, 1784, 1722 and 1695cm-1.

Workup

  1. temperatureto reflux for 10h
  2. temperatureThe mixture was cooled
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-254adb1d542048d888026e2e6d8f3955
Source dataset
uspto-grants-2000_02
Patent number
US06020329

Reaction notes

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