3-Phenylpropyl isothiocynate → HCID 86757394, compound

HRID 1596206Notes

Reaction equation

HRID 1596206 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1)[NH:5][C:6](=[O:22])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13].[C:32]1([CH2:38][CH2:39][CH2:40][N:41]=[C:42]=[S:43])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:42]([NH:41][CH2:40][CH2:39][CH2:38][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[S:43])=[CH:26][CH:25]=1)[NH:5][C:6](=[O:22])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:13])=[O:14]

Participants

4

Reactant 2

HCID 758153-Phenylpropyl isothiocynateHCID 18338281HCID 18338281, compound

Product 1

HCID 86757394HCID 86757394, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

An equimolar solution of N-(toluene-4-sulfonyl)-L-prolyl-4-amino-L-phenylalanine methyl ester and 3-phenylpropyl isothiocyanate in toluene was stirred at room temperature for 16 hr. The solvent was stripped off giving an amber oil which was submitted to preparatory HPLC (Waters silica cartridge; 85/15 CH2Cl2/EtOAc) for purification. The fractions were collected and the solvent removed yielding the title compound as a white solid, mp=74-80° C.

Workup

  1. customgiving an amber oil which
  2. customwas submitted to preparatory HPLC (Waters silica cartridge; 85/15 CH2Cl2/EtOAc) for purification
  3. customThe fractions were collected
  4. customthe solvent removed

Sources & evidence

ORD record
ord-4e6b9cdefa73474c866b61c2f6e4e5d9
Source dataset
uspto-grants-2001_09
Patent number
US06291453B1

Reaction notes

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