Triethylamine → 2-(3-Fluoro-4-isocyanato-phenyl)-2-methyl-propionic acid methyl ester

HRID 1690576Notes

Reaction equation

HRID 1690576 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([F:14])[CH:8]=1)([CH3:6])[CH3:5].Cl[C:17](Cl)([O:19]C(=O)OC(Cl)(Cl)Cl)Cl.CCN(CC)CC>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:15])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([N:13]=[C:17]=[O:19])=[C:9]([F:14])[CH:8]=1)([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 686458042-(4-Amino-3-fluoro-phenyl)-2-methyl-propionic acid methyl ester

Product 1

HCID 866402682-(3-Fluoro-4-isocyanato-phenyl)-2-methyl-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In analogy to the procedure described in example 9.1, 2-(4-amino-3-fluoro-phenyl)-2-methyl-propionic acid methyl ester (Chung, Jae-Uk; Kim, Su Yeon; Lim, Ju-Ok; Choi, Hyun-Kyung; Kang, Sang-Uk; Yoon, Hae-Seok; Ryu, HyungChul; Kang, Dong Wook; Lee, Jeewoo; Kang, Bomi; Choi, Sun; Toth, Attila; Pearce, Larry V.; Pavlyukovets, Vladimir A.; Lundberg, Daniel J.; Blumberg, Peter M. Bioorganic & Medicinal Chemistry (2007), 15(18), 6043-6053) was reacted with triphosgene in the presence of Et3N in CH2Cl2 under reflux conditions for 16 h to give the title compound as brown oil which was used in the next step without further purification. MS: m/e=255.4 [M+NH4+].

Sources & evidence

ORD record
ord-ff8243a44e794774b82e12c79a710500
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

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