Hydrochloric Acid → HCID 178501242, compound

HRID 2249968Notes

Reaction equation

HRID 2249968 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][C@@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH2:11]1.[CH3:20][C:21]([S:24](Cl)=[O:25])([CH3:23])[CH3:22].Cl>C(OCC)(=O)C>[CH3:20][C:21]([S:24]([NH:9][C@@H:10]1[CH2:11][CH2:12][C@H:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:14][CH2:15]1)=[O:25])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 46868612-Methylpropane-2-sulfinyl chlorideHCID 178501209HCID 178501209, compound

Product 1

HCID 178501242HCID 178501242, compoundYield 109.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (272 mL) was added dropwise to a suspension of methyl cis-4-amino-1-cyclohexane carboxylate hydrochloride (7) (151 g, 0.78 mol) and 2-methylpropane-2-sulfinyl chloride (3) (120.8 g, 1.1 eq) in ethyl acetate (755 mL) at 6 to 9° C. The mixture was stirred for an hour at the same temperature and poured into diluted hydrochloric acid. The mixture was extracted with ethyl acetate (750 mL×2) and each of organic layers was washed with water, 5% aqueous solution of sodium bicarbonate, water and brine, successively. The solvent was concentrated under reduced pressure to obtain oily (14) (222.7 g, 109%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (750 mL×2)
  2. washeach of organic layers was washed with water, 5% aqueous solution of sodium bicarbonate, water and brine
  3. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0958d3f9a37c4ad6a515ff8e49f85068
Source dataset
uspto-grants-2008_01
Patent number
US07314950B2

Reaction notes

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