Sodium Hydroxide → HCID 67727693, compound

HRID 963080Notes

Reaction equation

HRID 963080 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][C:43]=1[Cl:44])[C:5]([NH:7][C@H:8]([C:19]1[N:23]2[C:24]3[S:38][C:37]([CH2:39][CH3:40])=[CH:36][C:25]=3[C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])=[N:27][CH2:28][C:22]2=[N:21][N:20]=1)[CH2:9][C:10]([O:12]C1CCCCC1)=[O:11])=[O:6].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:41]=[CH:42][C:43]=1[Cl:44])[C:5]([NH:7][C@H:8]([C:19]1[N:23]2[C:24]3[S:38][C:37]([CH2:39][CH3:40])=[CH:36][C:25]=3[C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])=[N:27][CH2:28][C:22]2=[N:21][N:20]=1)[CH2:9][C:10]([OH:12])=[O:11])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86752708HCID 86752708, compound

Product 1

HCID 67727693HCID 67727693, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cyclohexyl (S)-(+)-3-(3,4-dichlorobenzoylamino)-3-(4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-9-yl)propionate (0.40 g) obtained in Example 270 was dissolved in methanol (5 ml). A 2N aqueous sodium hydroxide solution (0.6 ml) was added, and the mixture was stirred for 3 hours. The solvent was evaporated. Water was added and the mixture was washed with ethyl acetate. Citric acid was added to the aqueous layer to make the layer acidic. The mixture was extracted with ethyl acetate and the extract was dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography using a mixed solvent of chloroform, methanol and acetic acid as an eluent to give 96 mg of (S)-(+)-3-(3,4-dichlorobenzoylamino)-3-(4-(2-chlorophenyl)-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-9-yl)propionic acid.

Workup

  1. customThe solvent was evaporated
  2. additionWater was added
  3. washthe mixture was washed with ethyl acetate
  4. additionCitric acid was added to the aqueous layer
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialthe extract was dried over magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-88ec6679d48b46dc83197ba880541ef5
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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