4-Chlorophenyl Isocyanate → HCID 86604158, compound

HRID 1816870Notes

Reaction equation

HRID 1816870 reaction equation
[NH2:1][C@@H:2]([C:10](=[O:25])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][C:19]2=[O:24])=[CH:14][CH:13]=1)[CH2:3][P:4](=[O:9])([O:7][CH3:8])[O:5][CH3:6].[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][CH:28]=1>ClCCl>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:35])[NH:1][C@H:2]([CH2:3][P:4]([O:5][CH3:6])([O:7][CH3:8])=[O:9])[C:10]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][C:19]3=[O:24])=[CH:16][CH:17]=2)=[O:25])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 86604156HCID 86604156, compound

Product 1

HCID 86604158HCID 86604158, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.4 The solution of 0.2 g (0.54 mmol) of dimethyl (S)-{2-amino-2-[4-(3-oxomorpholin-4-yl)phenylcarbamoyl]ethyl}phosphonate and 0.092 g (0.54 mmol) of 4-chlorophenyl isocyanate in 10 ml of dichloromethane is stirred at room temperature for 12 hours. The methylene chloride solution is subsequently washed successively with 10 ml of each of 1N hydrochloric acid, saturated sodium hydrogencarbonate solution and water and dried over sodium sulfate. After the solvent has been stripped off, 10 ml of diethyl ether are added to the residue, and the white precipitate deposited is filtered off, giving 0.28 g (100%) of (S)-2-[3-(4-chlorophenyl)ureido]-N-[4-(3-oxomorpholin-4-yl)phenyl]-3-(dimethoxyphosphoryl)propionamide (“1D”), ESI 525.

Workup

  1. washThe methylene chloride solution is subsequently washed successively with 10 ml of each of 1N hydrochloric acid, saturated sodium hydrogencarbonate solution and water
  2. dry with materialdried over sodium sulfate
  3. addition10 ml of diethyl ether are added to the residue
  4. filtrationthe white precipitate deposited is filtered off

Sources & evidence

ORD record
ord-53d880317f8844c4886300d5a5deb433
Source dataset
uspto-grants-2009_10
Patent number
US07598241B2

Reaction notes

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