Potassium Hydroxide → 2-(2-Tritylaminothiazol-4-yl)-2-[(2-t-butoxycarbonylprop-2-yl)-oxyimino]-acetic acid

HRID 1577646Notes

Reaction equation

HRID 1577646 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:32][O:33][C:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])([CH3:36])[CH3:35])[C:27]([O:29]CC)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CO>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:32][O:33][C:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])([CH3:35])[CH3:36])[C:27]([OH:29])=[O:28])[N:25]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54508061Ethyl 2-(2-tritylamino-4-thiazolyl)-2-(1-tert.-butoxycarbonyl-1-methylethyl oxyimino)-acetate

Product 1

HCID 534453442-(2-Tritylaminothiazol-4-yl)-2-[(2-t-butoxycarbonylprop-2-yl)-oxyimino]-acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.2 g of the product of Step A, 2 ml of methanolic 1 N potassium hydroxide solution and 4 ml of methanol was refluxed for 2 hours and was then cooled during which 390 mg of the starting material crystallized which meant 810 mg of the starting product was saponified. The mixture was filtered and the filtrate was evaporated to dryness. The residue was taken up in 1 ml of dimethylformamide and 2 ml of N hydrochloric acid solution (pH=2). The mixture was stirred and 10 ml of water were added thereto. The mixture was extracted with methylene chloride and the organic phase was washed with water. The wash waters were extracted with methylene chloride and the combined organic phases were dried and vacuum filtered. The filtrate was evaporated and the oil residue was taken up in 4 ml of chloroform. The solution was diluted with 30 ml of ether and crystallization was effected. After 30 minutes with stirring, the mixture was vacuum filtered and the product was rinsed with ether and dried to obtain 472 mg of the syn isomer of 2-(2-tritylamino-4-thiazolyl)-2-(1-tert.-butoxycarbonyl-1-methylethyloxyimino)-acetic acid melting at 190° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customcrystallized which
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated to dryness
  5. addition10 ml of water were added
  6. extractionThe mixture was extracted with methylene chloride
  7. washthe organic phase was washed with water
  8. extractionThe wash waters were extracted with methylene chloride
  9. customthe combined organic phases were dried
  10. filtrationvacuum filtered
  11. customThe filtrate was evaporated
  12. additionThe solution was diluted with 30 ml of ether and crystallization
  13. stirringAfter 30 minutes with stirring
  14. filtrationfiltered
  15. washthe product was rinsed with ether
  16. customdried

Sources & evidence

ORD record
ord-dbf05ef75c8e4a31b2e892e3ac0a011c
Source dataset
uspto-grants-1981_09
Patent number
US04288434

Reaction notes

Loading…