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

HRID 1904634Notes

Reaction equation

HRID 1904634 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-4e4353bd8f7547899d389454002556e5
Source dataset
uspto-grants-1989_06
Patent number
US04839367

Reaction notes

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