Hydrochloric Acid → rel-Ethyl (1R,3S,4S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[(methylsulfonyl)oxy]cyclohexanecarboxylate

HRID 459508Notes

Reaction equation

HRID 459508 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C@@H:14]([OH:15])[CH2:13][CH2:12][C@@H:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].Cl>ClCCl>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C@@H:14]([O:15][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:13][CH2:12][C@@H:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66776719HCID 66776719, compound

Product 1

HCID 86593058rel-Ethyl (1R,3S,4S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[(methylsulfonyl)oxy]cyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

After ethyl (1R*,3S*,4S*)-3-tert-butoxycarbonylamino-4-hydroxycyclohexane-1-carboxylate (16 g) and triethylamine (38 ml) were dissolved in dichloromethane (150 ml), and the solution was cooled to −78° C., methanesulfonyl chloride (13 ml) was added dropwise at the same temperature. After stirring for 15 minutes at the same temperature, the mixture was heated to 0° C. and stirred for 30 minutes and then 2 hours at room temperature. After 0.1N hydrochloric acid was added, and the mixture was diluted with dichloromethane, the resultant organic layer was separated, washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain crude ethyl (1R*,3S*,4S*)-3-tert-butoxycarbonylamino-4-methanesulfonyloxycyclohexane-1-carboxylate.

Workup

  1. temperaturethe mixture was heated to 0° C.
  2. stirringstirred for 30 minutes
  3. custom2 hours
  4. customat room temperature
  5. customthe resultant organic layer was separated
  6. washwashed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-714cefef2d7444ec9a7c0668962c2b6a
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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