Hydrochloric Acid → HCID 44320227, compound

HRID 1706046Notes

Reaction equation

HRID 1706046 reaction equation
C([S:4][CH2:5][CH2:6][C:7]([C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[C:15]([OH:17])=[O:16])=[O:8])(=O)C.[OH-].[NH4+].Cl>O>[SH:4][CH2:5][CH2:6][C:7]([C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[C:15]([OH:17])=[O:16])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 53993919HCID 53993919, compound

Product 1

HCID 44320227HCID 44320227, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

trans-2-[3-(Acetylthio)-1-oxopropyl]cyclohexanecarboxylic acid (3.0 g., 11.6 mmol.) is added to a cold mixture of 5 ml. of concentrated ammonium hydroxide and 5 ml. of water under argon. The mixture is stirred at room temperature for 30 minutes. While cooling to 0°, the solution is acidified with concentrated hydrochloric acid. The mixture is extracted four times with ethyl acetate. The extracts are dried and the solvent is removed in vacuo. The oily product is chromatographed on 90 g. of silica gel eluting with ethyl acetate. A total of 2.2 g. (88%) of material is obtained which is contaminated with some more polar material. Chromatography of 1.9 g. of this material on 60 g. of silica gel and eluting with chloroform and 2% methanol in chloroform gives 1.4 g. of trans-2-(3-mercapto-1-oxopropyl)cyclohexanecarboxylic acid, recrystallized from isopropyl ether-hexane, 1.0 g. (46%), m.p. 71°-74°.

Workup

  1. temperatureWhile cooling to 0°
  2. extractionThe mixture is extracted four times with ethyl acetate
  3. customThe extracts are dried
  4. customthe solvent is removed in vacuo
  5. customThe oily product is chromatographed on 90 g

Sources & evidence

ORD record
ord-20874de30b874c9cb140c453aeda6fe7
Source dataset
uspto-grants-1980_06
Patent number
US04206137

Reaction notes

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