Phenoxyacetic Acid → HCID 54113420, compound

HRID 1439354Notes

Reaction equation

HRID 1439354 reaction equation
[CH3:1][C:2]1([CH3:24])[CH:6]([C:7]([O-:9])=[O:8])[N:5]2[C:10](=[O:23])[C@@H:11]([NH:12][C:13](=[O:22])[CH2:14][O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@H:4]2[S:3]1.[K+].O(CC(O)=O)C1C=CC=CC=1.[C:37]1([C:43]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[N+]=[N-])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>O.ClCCl>[CH3:1][C:2]1([CH3:24])[CH:6]([C:7]([O:9][CH:43]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:8])[N:5]2[C:10](=[O:23])[C@@H:11]([NH:12][C:13](=[O:22])[CH2:14][O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@H:4]2[S:3]1

Participants

6

Reactant 3

HCID 19188Phenoxyacetic AcidHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 23689977HCID 23689977, compound

Product 1

HCID 54113420HCID 54113420, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of potassium (5R,6R)-2,2-dimethyl-6-phenoxyacetamidopenam-3-carboxylate (10 g, 25.7 mM) and phenoxyacetic acid (2 g, 13.1 mM) in water (100 ml) was added a solution of diphenyldiazomethane (5.2 g, 27 mM) in dichloromethane (100 ml). The pH was adjusted to 4.0 and the mixture stirred for 10 minutes. After separation, the solvent was washed with water (100 ml), 5% w/v sodium bicarbonate solution (100 ml) and water (100 ml). The solvent was removed in vacuo to give the title compound (11.4 g).

Workup

  1. customAfter separation
  2. washthe solvent was washed with water (100 ml), 5%
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0392af235a244eb7ba1613008f2bb2f9
Source dataset
uspto-grants-1977_11
Patent number
US04059573

Reaction notes

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