1,2-Dichloro-4-(isocyanatomethyl)benzene → HCID 86661309, compound

HRID 1685074Notes

Reaction equation

HRID 1685074 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:14](=[O:16])[CH3:15])[CH2:10][C@@H:9]1[C:17]1[N:18]=[C:19]([NH2:22])[S:20][CH:21]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:23][C:24]1[CH:25]=[C:26]([CH:31]=[CH:32][C:33]=1[Cl:34])[CH2:27][N:28]=[C:29]=[O:30]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:14](=[O:16])[CH3:15])[CH2:10][C@@H:9]1[C:17]1[N:18]=[C:19]([NH:22][C:29]([NH:28][CH2:27][C:26]2[CH:31]=[CH:32][C:33]([Cl:34])=[C:24]([Cl:23])[CH:25]=2)=[O:30])[S:20][CH:21]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 27333681,2-Dichloro-4-(isocyanatomethyl)benzeneHCID 86661310HCID 86661310, compound

Product 1

HCID 86661309HCID 86661309, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-4-Acetoxy-2-(2-amino-thiazol-4-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (327 mg, 1 mmol) was combined with 3,4-dichlorobenzyl isocyanate (303 mg, 1.5 mmol) in DCM (10 mL) and stirred overnight. The reaction mixture was concentrated and purified by chromatography (silica gel, DCM/MeOH/NH4OH) to afford (R)-4-acetoxy-2-{2-[3-(3,4-dichloro-benzyl)-ureido]-thiazol-4-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by chromatography (silica gel, DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-ecb81b24c85b415b981a8e9763bb720e
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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