Hydrochloric Acid → HCID 70562217, compound

HRID 2287183Notes

Reaction equation

HRID 2287183 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[S:27]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=[O:29])=[O:28])([O:3]C)=[O:2].[OH-].[Na+].C(OCC)(=O)C.Cl>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[S:27]([CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)(=[O:28])=[O:29])([OH:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 70563215HCID 70563215, compound

Product 1

HCID 70562217HCID 70562217, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 756 mg of benzyl α-(3ξ-carbomethoxy-2-phenylmethanesulfonyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]-heptan-6-yl)-α-isopropylideneacetate dissolved in a mixture of 9 ml of acetone and 2.7 ml of water is added 1.85 ml of 1.012 N aqueous solution of sodium hydroxide under ice-cooling. After 15 minutes, the reaction mixture is poured into ice water, mixed with ethyl acetate, adjusted to pH 2 with 2 N-hydrochloric acid under ice-cooling and extracted with ethyl acetate. The extract is washed with water, dried on sodium sulfate, and evaporated under reduced pressure to yield 705 mg of benzyl α-(3ξ-carboxy-2-phenylmethanesulfonyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with water
  5. customdried on sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4e8dfe3513e74d82887e471549a43ce9
Source dataset
uspto-grants-1981_05
Patent number
US04269773

Reaction notes

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