Ammonia → HCID 86630138, compound

HRID 656216Notes

Reaction equation

HRID 656216 reaction equation
[C:1]([O:5][C:6](=[O:35])[N:7]([C@@H:10]1[CH2:15][CH2:14][CH2:13][C@@H:12]([S:16]CC2C(C)=CC(C)=CC=2C)[C@@H:11]1[O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2].N.[Na].[Cl-].[NH4+]>O1CCCC1>[C:1]([O:5][C:6](=[O:35])[N:7]([C@@H:10]1[CH2:15][CH2:14][CH2:13][C@@H:12]([SH:16])[C@@H:11]1[O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:29])[CH3:30])[CH2:8][CH3:9])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 86630136HCID 86630136, compound

Product 1

HCID 86630138HCID 86630138, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of [(1R,2R,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(2,4,6-trimethyl-benzylsulfanyl)-cyclohexyl]-ethyl-carbamic acid tert-butyl ester+(1S,2S,3S) diastereomer (1.20 g, 2.30 mmol) in 10 ml of tetrahydrofuran and 20 ml of liquid ammonia was treated at −78° C. under an argon atmosphere with sodium (106 mg, 4.60 mmol) and stirred at −78° C. for one hour. Then solid ammonium chloride was added and the reaction mixture was warmed to room temperature, diluted with tetrahydrofuran and flushed with nitrogen. The residual mixture was filtered and concentrated under reduced pressure to yield crude [(1R,2R,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-mercapto-cyclohexyl]-ethyl-carbamic acid tert-butyl ester+(1S,2S,3S) diastereomer (quantitative yield) which was directly used for the next step.

Workup

  1. temperaturethe reaction mixture was warmed to room temperature
  2. customflushed with nitrogen
  3. filtrationThe residual mixture was filtered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b9dccbb8f47b46c7b4650a3d99a63125
Source dataset
uspto-grants-2011_12
Patent number
US08071643B2

Reaction notes

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