1-Isocyanato-3,5-dimethoxybenzene → 1-[(S)-3-[3-(4-chloro-phenoxy)-azetidin-1-yl]-1-hydroxymethyl-propyl)-3-(3,5-dimethoxy-phenyl)-urea

HRID 1182129Notes

Reaction equation

HRID 1182129 reaction equation
[NH2:1][C@@H:2]([CH2:5][CH2:6][N:7]1[CH2:10][CH:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:8]1)[CH2:3][OH:4].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([N:29]=[C:30]=[O:31])[CH:24]=[C:25]([O:27][CH3:28])[CH:26]=1>ClCCl>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([O:11][CH:9]2[CH2:10][N:7]([CH2:6][CH2:5][C@H:2]([NH:1][C:30]([NH:29][C:23]3[CH:22]=[C:21]([O:20][CH3:19])[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=3)=[O:31])[CH2:3][OH:4])[CH2:8]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 27362001-Isocyanato-3,5-dimethoxybenzeneHCID 11184815(S)-2-amino-4-[3-(4-chlorophenoxy)-azetidin-1-yl]-butan-1-ol

Product 1

HCID 102384451-[(S)-3-[3-(4-chloro-phenoxy)-azetidin-1-yl]-1-hydroxymethyl-propyl)-3-(3,5-dimethoxy-phenyl)-urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-2-amino-4-[3-(4-chloro-phenoxy)-azetidin-1-yl]-butan-1-ol (0.2 g, 0.74 mmol) in dichloromethane (6 ml) is treated with 3,5-dimethoxy-phenyl-isocyanate (0.12 g, 0.667 mmol). The reaction mixture is stirred at ambient temperature for 24 hours and then evaporated. The crude product is purified by flash silica chromatography (elution gradient 3:97 to 7:93 methanol/dichloromethane) to afford 1-{(S)-3-[3-(4-chloro-phenoxy)-azetidin-1-yl]-1-hydroxymethyl-propyl}-3-(3,5-dimethoxy-phenyl)-urea. [MH]+ 449.9.

Workup

  1. customevaporated
  2. customThe crude product is purified by flash silica chromatography (elution gradient 3:97 to 7:93 methanol/dichloromethane)

Sources & evidence

ORD record
ord-1a55fa0a9e2f4f3798acc240cafc2499
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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