Phenyl isocyanate → HCID 69817779, compound

HRID 2417423Notes

Reaction equation

HRID 2417423 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([N:12]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:13][C@H:14]([OH:23])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][OH:11])=[CH:4][CH:3]=1.[C:31]1([N:37]=[C:38]=[O:39])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>ClCCl.N>[CH2:24]([N:12]([C@H:9]([CH2:10][OH:11])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:38]([NH:37][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:39])=[CH:3][CH:4]=1)[CH2:13][C@H:14]([OH:23])[CH2:15][O:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 69817666HCID 69817666, compound

Product 1

HCID 69817779HCID 69817779, compound

Reagents, catalysts & solvents 2

HCID 222AmmoniaCatalystHCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of (2S)-3-(4-aminophenyl)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-1-propanol (76 mg) in dichloromethane (0.8 ml) was added dropwise phenyl isocyanate (0.022 ml), and the mixture was stirred at the same temperature for 40 minutes. One drop of 28% ammonia solution was added to the mixture, the mixture was concentrated, and the residue was purified by column chromatography (silica gel, chloroform/methanol) to give N-[4-[(2S)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]-amino]-3-hydroxypropyl]phenyl]-N′-phenylurea (89 mg) as a white amorphous powder.

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue was purified by column chromatography (silica gel, chloroform/methanol)

Sources & evidence

ORD record
ord-8efc2be9371e4aa7a69c42f708706723
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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