Sodium Bicarbonate → HCID 118107726, compound

HRID 1053831Notes

Reaction equation

HRID 1053831 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][CH2:9][C@@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]([N:18]2[CH2:22][C@@H:21]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH2:20][C@H:19]2[C:29]([NH:31][C:32]2[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=2)=[O:30])=[O:17])[CH2:12][CH2:11]1)=[O:7])([CH3:4])[CH3:3].[N-:42]=[C:43]=[O:44].[K+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.O>[C:2]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([C:16]([N:18]2[CH2:22][C@@H:21]([N:23]3[CH2:28][CH2:27][N:26]([C:43](=[O:44])[NH2:42])[CH2:25][CH2:24]3)[CH2:20][C@H:19]2[C:29]([NH:31][C:32]2[CH:33]=[CH:34][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:40][CH:41]=2)=[O:30])=[O:17])[CH2:12][CH2:11]1)=[O:7])([CH3:1])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 11051572Potassio isocyanateHCID 178498179HCID 178498179, compound

Product 1

HCID 118107726HCID 118107726, compoundYield 33.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of the compound prepared in Example 50 (150 mg) in acetic acid (2 mL) and water (2 mL) was added potassium isocyanate (105 mg) and the mixture stirred at room temperature for 4 days. The reaction mixture was then treated with saturated aqueous sodium bicarbonate (10 mL) and extracted into dichloromethane (3×10 mL). The combined organic phases were washed with brine, dried and concentrated. Purification by flash chromatography (silica gel, 5-10% methanol/dichloromethane) gave methyl 4-[(2S,4S)-1-{[4-({[(tert-butoxy)carbonyl]amino}methyl)cyclohexyl]carbonyl}-4-(4-carbamoylpiperazin-1-yl)pyrrolidine-2-amido]benzoate (54 mg) as a colourless oil.

Workup

  1. extractionextracted into dichloromethane (3×10 mL)
  2. washThe combined organic phases were washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customPurification by flash chromatography (silica gel, 5-10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-e91d5d4933e84a25b288c76601f4f7a0
Source dataset
uspto-grants-2016_07
Patent number
US09394250B2

Reaction notes

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