Ethyl bromoacetate → {4-Chloro-3-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(4-methyl-3-oxo-3,4-dihydro-2h-benzo[1,4]oxazin-6-yl)-propyl]-phenoxy}-acetic acid ethyl ester

HRID 2096718Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH:9]([CH3:28])[C:10]([C:16]1[CH:17]=[CH:18][C:19]2[O:24][CH2:23][C:22](=[O:25])[N:21]([CH3:26])[C:20]=2[CH:27]=1)([OH:15])[C:11]([F:14])([F:13])[F:12].[CH2:29]([O:31][C:32](=[O:35])[CH2:33]Br)[CH3:30].C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH2:29]([O:31][C:32](=[O:35])[CH2:33][O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH:9]([CH3:28])[C:10]([OH:15])([C:16]2[CH:17]=[CH:18][C:19]3[O:24][CH2:23][C:22](=[O:25])[N:21]([CH3:26])[C:20]=3[CH:27]=2)[C:11]([F:12])([F:13])[F:14])[CH:4]=1)[CH3:30]

Participants

Reactant 3

HCID 7748Ethyl bromoacetate

HCID 10796Cesium carbonate

HCID 666971956-[2-(2-Chloro-5-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-methyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 66697310{4-Chloro-3-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(4-methyl-3-oxo-3,4-dihydro-2h-benzo[1,4]oxazin-6-yl)-propyl]-phenoxy}-acetic acid ethyl ester

Procedure

In analogy to Example 1, step 5, 6-[2-(2-chloro-5-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-methyl-4H-benzo[1,4]oxazin-3-one (Example 1, step 4) was reacted with ethylbromoacetate and cesium carbonate to give the title compound as a colorless solid. MS (m/e, ISP neg. ion)=500.2 [M−H+].

Sources & evidence

ORD record: ord-f8f423a7616946dbbea9f5aefebfe272
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450313B2

Reaction notes

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