Sodium Hydroxide → HCID 70561159, compound

HRID 971410Notes

Reaction equation

HRID 971410 reaction equation
[C:1]([CH:5]1[O:11][CH:10]2[CH:7]([C:8](=[O:26])[N:9]2[C:12](=[C:23]([CH3:25])[CH3:24])[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[N:6]1[C:27](=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([O:3]C)=[O:2].[OH-].[Na+]>CC(C)=O.O>[C:1]([CH:5]1[O:11][CH:10]2[CH:7]([C:8](=[O:26])[N:9]2[C:12](=[C:23]([CH3:25])[CH3:24])[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[N:6]1[C:27](=[O:34])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70561454HCID 70561454, compound

Product 1

HCID 70561159HCID 70561159, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a solution of 7.02 g of benzyl α-(3ξ-carbomethoxy-2-benzoyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate dissolved in a mixture of 85 ml of acetone and 26.5 ml of water is added 20 ml of 1.012 N aqueous solution of sodium hydroxide at -3° to -4° C. over a period of an hour and the mixture diluted with water and washed with ethyl acetate. The aqueous layer is separated, adjusted to pH 2.0 with 4 N hydrochloric acid, and then extracted with ethyl acetate. The extract is washed with water, dried on sodium sulfate, and concentrated under reduced pressure to yield 6.34 g of benzyl α-(3ξ-carboxy-2-benzoyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate as foamy material.

Workup

  1. washwashed with ethyl acetate
  2. customThe aqueous layer is separated
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with water
  5. customdried on sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cddc7bfff5cd48629a28e93521903cef
Source dataset
uspto-grants-1979_07
Patent number
US04159984

Reaction notes

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