Phenyl isocyanate → N-(3-Phenylcarbamoylthio-2-methyl-propanoyl)-N-cyclopentyl glycine

HRID 2164781Notes

Reaction equation

HRID 2164781 reaction equation
[SH:1][CH2:2][CH:3]([CH3:16])[C:4]([N:6]([CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:7][C:8]([OH:10])=[O:9])=[O:5].[C:17]1([N:23]=[C:24]=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl.CCOCC>[C:17]1([NH:23][C:24]([S:1][CH2:2][CH:3]([CH3:16])[C:4]([N:6]([CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:7][C:8]([OH:10])=[O:9])=[O:5])=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 13469595(S)-[Cyclopentyl-(3-mercapto-2-methyl-propionyl)-amino]-acetic acid

Product 1

HCID 13469596N-(3-Phenylcarbamoylthio-2-methyl-propanoyl)-N-cyclopentyl glycine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4.9 g (0.02M) of N-(3-mercapto-2-methyl propanoyl)-N-cyclopentyl glycine and 8 ml of phenyl isocyanate in 5 ml methylene chloride was stirred at room temperature for 72 hours. The mixture was diluted with ether and filtered. The ether solution was washed with water, dried over MgSO4 and evaporated to dryness. The crude residue was dissolved in acetonitrile, treated with charcoal and crystallized by addition of ether, m.p. 170°-172° C.

Workup

  1. filtrationfiltered
  2. washThe ether solution was washed with water
  3. dry with materialdried over MgSO4
  4. customevaporated to dryness
  5. dissolutionThe crude residue was dissolved in acetonitrile
  6. additiontreated with charcoal
  7. customcrystallized by addition of ether, m.p. 170°-172° C.

Sources & evidence

ORD record
ord-3ac4fe4686914f99bcccb03a55a98552
Source dataset
uspto-grants-1985_03
Patent number
US04507316

Reaction notes

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