Water → HCID 178453889, compound

HRID 1663234Notes

Reaction equation

HRID 1663234 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][CH2:16]OS(C)(=O)=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1.O>C(#N)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][CH2:16][N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 178453928HCID 178453928, compound

Product 1

HCID 178453889HCID 178453889, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methanesulfonic acid trans-2-(4-tert-butoxycarbonylamino-cyclohexyl)-ethyl ester (3.2 g, 10 mmol), potassium carbonate (1.4 g, 10 mmol) and pyrrolidine (1.25 mL, 15 mmol) in acetonitrile (40 mL) was stirred at 60° C. for 2 hours. The mixture was cooled to room temperature and poured into water (200 mL). The precipitated white crystals were filtered off and washed with water to yield 1.9 g (64%) of the title compound.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe precipitated white crystals were filtered off
  3. washwashed with water

Sources & evidence

ORD record
ord-5fa46e2ecce5411783146404453a30f0
Source dataset
uspto-grants-2011_10
Patent number
US08034827B2

Reaction notes

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