Triphosgene → (S)-1-Bromo-4-(1-isocyanato-ethyl)-2-methyl-benzene

HRID 1191887Notes

Reaction equation

HRID 1191887 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH2:10])[CH3:9])=[CH:4][C:3]=1[CH3:11].Cl[C:13](Cl)([O:15]C(=O)OC(Cl)(Cl)Cl)Cl.C1(C2(CC(O)(C)C)OC(=O)N([C@H](C3C=CC(C4C=CN(C)C(=O)C=4)=CC=3)C)CC2)CC1>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]=[C:13]=[O:15])[CH3:9])=[CH:4][C:3]=1[CH3:11]

Participants

5

Reactant 3

HCID 94429TriphosgeneHCID 58102381(S)-1-(4-Bromo-3-methylphenyl)ethan-1-amineHCID 596356736-cyclopropyl-6-(2-hydroxy-2-methylpropyl)-3-((S)-1-(4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl)ethyl)-1,3-oxazinan-2-one

Product 1

HCID 86649416(S)-1-Bromo-4-(1-isocyanato-ethyl)-2-methyl-benzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared from (S)-1-(4-bromo-3-methyl-phenyl)-ethylamine and triphosgene following a procedure analogous to that described in Step 4 of Intermediate 1. Mass spectrum (ESI+): m/z=272/274 (Br) [M+H+MeOH]+.

Sources & evidence

ORD record
ord-2002a9b37d8647b3a82208886d7de198
Source dataset
uspto-grants-2014_03
Patent number
US08680093B2

Reaction notes

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