Potassium Carbonate → HCID 21968288, compound

HRID 1066055Notes

Reaction equation

HRID 1066055 reaction equation
[NH2:1][C@H:2]([C:10]([CH:12]([C:14]([CH:16]([Cl:28])[C:17](=[O:27])[C@H:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH2:19])=[O:15])[Cl:13])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:29](=[O:32])([O-])[O-].[K+].[K+].[CH:35]1([C:41](Cl)=[O:42])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>C(Cl)Cl.O>[CH:35]1([C:41]([NH:19][C@H:18]([C:17]([CH:16]([C:14]([CH:12]([Cl:13])[C:10](=[O:11])[C@H:2]([CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:1][C:29]([CH:4]2[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)=[O:32])=[O:15])[Cl:28])=[O:27])[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:42])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 75938Cyclohexanecarbonyl chlorideHCID 86755362HCID 86755362, compound

Product 1

HCID 21968288HCID 21968288, compoundYield 162.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

A cooled (−10° C.) mixture containing L-phenylalanylchloromethylketone (3.2 mmole) in CH2Cl2 (30 ml) and potassium carbonate (10 mmole) in water (10 ml) was treated with cyclohexanecarbonylchloride (3.2 mmole). The resulting mixture was stirred for two hours at ambient temperature. The organic layer was separated, washed with water (3×20 ml) and dried over anhydrous magnesium sulfate. Filtration and concentration in vacuo gave the titled compound as a cream colored solid (2.6 mmole, 81%).

Workup

  1. customThe organic layer was separated
  2. washwashed with water (3×20 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-64eea38a83cf40ffb6113594ddc0a3f2
Source dataset
uspto-grants-2001_06
Patent number
US06242448B1

Reaction notes

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