Sodium Hydroxide → HCID 53899458, compound

HRID 1378028Notes

Reaction equation

HRID 1378028 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]CC)=[O:17])[N:14]=[CH:15][N:7]2[C:6]2[CH:21]=[CH:22][S:23][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:21]=[CH:22][S:23][C:5]1=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53981632HCID 53981632, compound

Product 1

HCID 53899458HCID 53899458, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

13.9 ml (55.6 mmol) of 4N sodium hydroxide solution were added dropwise to a suspension of 13.5 g (44.5 mmol) of ethyl (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. The mixture was heated at reflux for 30 minutes and the ethanol was subsequently distilled off. The aqueous phase was washed twice with methylene chloride and adjusted to pH=3 with 4N hydrochloric acid. The resulting precipitate was filtered off and 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 of m.p. 260° (dec.).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 30 minutes
  3. distillationthe ethanol was subsequently distilled off
  4. washThe aqueous phase was washed twice with methylene chloride
  5. filtrationThe resulting precipitate was filtered off
  6. washwashed with water, ethanol and subsequently with diethyl ether

Sources & evidence

ORD record
ord-242cc6b7b3064886ad6b72c8fe4c03bd
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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