Thiophosgene → HCID 86743375, compound

HRID 1607712Notes

Reaction equation

HRID 1607712 reaction equation
[C:1](Cl)(Cl)=[S:2].[NH2:5][CH:6]1[C:12](=[O:13])[N:11]2[CH:7]1[S:8][C:9]([CH3:31])([CH3:30])[CH:10]2[C:14]([O:16][CH:17]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].C([O-])(=O)C.[NH4+:36].[OH-].[NH4+]>C(OCC)(=O)C.O>[NH2:36][C:1]([NH:5][CH:6]1[C:12](=[O:13])[N:11]2[CH:7]1[S:8][C:9]([CH3:31])([CH3:30])[CH:10]2[C:14]([O:16][CH:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:15])=[S:2]

Participants

7

Reactant 4

HCID 10040ThiophosgeneHCID 14923Ammonium HydroxideHCID 517165Ammonium AcetateHCID 12916811HCID 12916811, compound

Product 1

HCID 86743375HCID 86743375, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 0.9 ml portion of thiophosgene was added to a stirred mixture of 5.55 g of 6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, diphenylmethyl ester in 100 ml of ethyl acetate and 5.0 g of ammonium acetate in 50 ml of water. After stirring for 10-15 minutes concentrated ammonium hydroxide was added in increments over 5 hours. The layers were separated and the organic layer washed twice with brine, dried, evaporated to about 20 ml and chilled. The solid was collected, giving 2.385 g of the desired compound.

Workup

  1. additionwas added in increments over 5 hours
  2. customThe layers were separated
  3. washthe organic layer washed twice with brine
  4. customdried
  5. customevaporated to about 20 ml
  6. temperaturechilled
  7. customThe solid was collected

Sources & evidence

ORD record
ord-7ae5a61933c441d7b3536ae21dad6c6a
Source dataset
uspto-grants-1989_09
Patent number
US04866169

Reaction notes

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