Sodium Hydroxide → HCID 53899458, compound

HRID 1737340Notes

Reaction equation

HRID 1737340 reaction equation
[OH-].[Na+].[O:3]=[C:4]1[N:10]2[CH2:11][CH2:12][C@H:9]2[C:8]2=[C:13]([C:16]([O-:18])=[O:17])[N:14]=[CH:15][N:7]2[C:6]2[CH:19]=[CH:20][S:21][C:5]1=2>C(O)C.O>[O:3]=[C:4]1[N:10]2[CH2:11][CH2:12][C@H:9]2[C:8]2=[C:13]([C:16]([OH:18])=[O:17])[N:14]=[CH:15][N:7]2[C:6]2[CH:19]=[CH:20][S:21][C:5]1=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86753947HCID 86753947, compound

Product 1

HCID 53899458HCID 53899458, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

13.9 ml (0.0556 mol) of 4N sodium hydroxide solution were added dropwise to a suspension of 13.5 g (0.0445 mol) of (S)-8-oxo-11,11a-dihydro-8H,10H-azeto[1,2-a]imidazo[5,1-c]thieno[3,2-e][1,4]diazepine-1-carboxylate in 10 ml of ethanol and 16 ml of water and the mixture was heated at reflux for 1/2 hr. Subsequently, the ethanol was distilled off. The aqueous phase was washed twice with dichloromethane and adjusted to pH=3 with 4N hydrochloric acid. The resulting precipitate was filtered off, washed with water, ethanol and subsequently with diethyl ether. There were obtained 10.8 g (88%) of (S)-8-oxo-11,11a-dihydro-8H,10H-azeto[1,2-a]imidazo[5,1-c]thieno[3,2-e][1,4]diazepine-1-carboxylic acid as a colourless powder; m.p. 260° (dec.).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1/2 hr
  3. distillationSubsequently, the ethanol was distilled off
  4. washThe aqueous phase was washed twice with dichloromethane
  5. filtrationThe resulting precipitate was filtered off
  6. washwashed with water, ethanol and subsequently with diethyl ether

Sources & evidence

ORD record
ord-0304c65db62949adbd61899c1c08df48
Source dataset
uspto-grants-1999_10
Patent number
US05962450

Reaction notes

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