Triethylamine → 3-(3-Fluoro-4-isocyanato-phenyl)-propionic acid tert-butyl ester

HRID 1690564Notes

Reaction equation

HRID 1690564 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([F:16])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:19](Cl)([O:21]C(=O)OC(Cl)(Cl)Cl)Cl.CCN(CC)CC>C(Cl)Cl>[C:1]([O:5][C:6](=[O:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]=[C:19]=[O:21])=[C:11]([F:16])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 66905628Tert-butyl 3-(4-amino-3-fluorophenyl)propanoate

Product 1

HCID 866402673-(3-Fluoro-4-isocyanato-phenyl)-propionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In analogy to the procedure described in example 9.1, 3-(4-amino-3-fluoro-phenyl)-propionic acid tert-butyl ester was reacted with triphosgene in the presence of Et3N in CH2Cl2 under reflux conditions for 20 h to give the title compound as yellow oil which was used in the next step without further purification. MS: m/e=265.1 [M+].

Sources & evidence

ORD record
ord-e95c33b171d949e58ecc0610fb2bd4ec
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

Loading…