Hydrochloric Acid → HCID 86736761, compound

HRID 482843Notes

Reaction equation

HRID 482843 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:38]([O:40]C)=[O:39])[CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]([C:34](=[O:37])[CH:35]=[O:36])[CH:20]2[CH2:23][N:22]([CH:24]([C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)[C:25]([OH:27])=[O:26])[C:21]2=[O:33])=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([O:5][C:6]([NH:8][CH:9]([C:38]([OH:40])=[O:39])[CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]([C:34](=[O:37])[CH:35]=[O:36])[CH:20]2[CH2:23][N:22]([CH:24]([C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)[C:25]([OH:27])=[O:26])[C:21]2=[O:33])=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 86736762HCID 86736762, compound

Product 1

HCID 86736761HCID 86736761, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[3-{4-(3-tert-butoxycarbonylamino-3-methoxycarbonylpropoxy)phenylglyoxyloylamino}-2-oxo-1-azetidinyl]-2-(2-thienyl)acetic acid (0.480 g.) was dissolved in methanol (3 ml.), and to the solution, there was added 1 N aqueous sodium hydroxide (2 ml.) under ice-cooling. The mixture was stirred at the same temperature for 7 hours while adjusting to pH 9.0 to 9.5 with 1 N aqueous sodium hydroxide. After the reaction, the reaction mixture was adjusted to pH 7.0 with dilute hydrochloric acid and evaporated to dryness under reduced pressure on a water bath. The resultant residue was dissolved in a small amount of water, and the aqueous solution was adjusted to pH 5.5 with dilute hydrochloric acid and then washed with ethyl acetate. The aqueous solution was adjusted to pH 4.0 to 4.5 with dilute hydrochloric acid and then extracted with ethyl acetate. This extract was evaporated to dryness under reduced pressure to give 2-[3-{4-(3-tert-butoxycarbonylamino-3-carboxypropoxy)phenylglyoxyloylamino}-2-oxo- 1-azetidinyl]-2-(2-thienyl)acetic acid (0.350 g.).

Workup

  1. temperaturecooling
  2. customAfter the reaction
  3. customevaporated to dryness under reduced pressure on a water bath
  4. dissolutionThe resultant residue was dissolved in a small amount of water
  5. washwashed with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. customThis extract was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-25d90799ec6a48f3b86c6ed68c06f24f
Source dataset
uspto-grants-1986_03
Patent number
US04576753

Reaction notes

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