Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) ester → HCID 23313851, compound

HRID 745614Notes

Reaction equation

HRID 745614 reaction equation
C([O:3][C:4]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:15])[CH:12]=2)[NH:7]1)=[O:5])C.C(=O)(O)[O-].[Na+].C([S:24][CH2:25][CH:26]([CH3:30])[C:27](Cl)=[O:28])(=O)C>C(Cl)Cl>[SH:24][CH2:25][CH:26]([CH3:30])[C:27]([N:7]1[C:8]2[C:13](=[CH:12][C:11]([OH:15])=[CH:10][CH:9]=2)[CH2:14][CH:6]1[C:4]([O-:3])=[O:5])=[O:28].[CH:8]1([NH2+:7][CH:6]2[CH2:4][CH2:27][CH2:26][CH2:25][CH2:14]2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) esterHCID 516892Sodium BicarbonateHCID 54199695HCID 54199695, compound

Product 1

HCID 23313851HCID 23313851, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the stirred solution of 1.8 g of 5-hydroxyindoline-2-carboxylic acid ethyl ester in 50 ml of methylene chloride, is added 1.5 g of solid sodium bicarbonate, followed by 1.6 g of 3-acetylthio-2-methylpropanoyl chloride during 1 minute. The mixture is stirred for 3 hours at room temperature, diluted with 100 ml of methylene chloride and washed with 50 ml of water, 50 ml of 1N hydrochloric acid and 50 ml of saturated aqueous sodium bicarbonate. The organic layer is dried, evaporated and the residue taken up in 20 ml of methanol. This solution, and 17 ml of 2.03N aqueous potassium hydroxide, are each deoxygenated by bubbling nitrogen through for 10 minutes. The latter solution is added to the former and the mixture stirred for 2 hours at room temperature. It is combined with 50 ml of 1N hydrochloric acid, extracted thrice with 50 ml of methylene chloride, the extract dried and evaporated at room temperature. The residue is converted to its dicyclohexylamine salt as described previously, to yield the dicyclohexylammonium 1-(3-mercapto-2-methylpropanoyl)-5-hydroxyindoline-2-carboxylate melting at 208°-211°.

Workup

  1. washwashed with 50 ml of water, 50 ml of 1N hydrochloric acid and 50 ml of saturated aqueous sodium bicarbonate
  2. customThe organic layer is dried
  3. customevaporated
  4. customeach deoxygenated
  5. customby bubbling nitrogen through for 10 minutes
  6. additionThe latter solution is added to the former and the mixture
  7. stirringstirred for 2 hours at room temperature
  8. extractionextracted thrice with 50 ml of methylene chloride
  9. customthe extract dried
  10. customevaporated at room temperature

Sources & evidence

ORD record
ord-0016af1aafa44f5b81f51931ef5c607d
Source dataset
uspto-grants-1986_07
Patent number
US04599357

Reaction notes

Loading…