Ethyl bromoacetate → {3'-Chloro-4-fluoro-4'-[3,3,3-trifluoro-2-(8-fluoro-4-methyl-3-oxo-3,4-dihydro-2h-benzo[1,4]oxazin-6-yl)-2-hydroxy-1-methyl-propyl]-biphenyl-3-yloxy}-acetic acid ethyl ester

HRID 2386735

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[C:31]([OH:36])[CH:30]=2)[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:28])[C:9]([C:15]1[CH:16]=[C:17]([F:27])[C:18]2[O:23][CH2:22][C:21](=[O:24])[N:20]([CH3:25])[C:19]=2[CH:26]=1)([OH:14])[C:10]([F:13])([F:12])[F:11].[CH2:37]([O:39][C:40](=[O:43])[CH2:41]Br)[CH3:38].C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH2:37]([O:39][C:40](=[O:43])[CH2:41][O:36][C:31]1[CH:30]=[C:29]([C:4]2[CH:5]=[CH:6][C:7]([CH:8]([CH3:28])[C:9]([C:15]3[CH:16]=[C:17]([F:27])[C:18]4[O:23][CH2:22][C:21](=[O:24])[N:20]([CH3:25])[C:19]=4[CH:26]=3)([OH:14])[C:10]([F:13])([F:11])[F:12])=[C:2]([Cl:1])[CH:3]=2)[CH:34]=[CH:33][C:32]=1[F:35])[CH3:38]

Participants

Reactant 3

HCID 7748Ethyl bromoacetate

HCID 10796Cesium carbonate

HCID 866458706-[2-(3-Chloro-4'-fluoro-3'-hydroxy-biphenyl-4-yl)-1-hydroxy-1-trifluoromethyl-propyl]-8-fluoro-4-methyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 75240040{3'-Chloro-4-fluoro-4'-[3,3,3-trifluoro-2-(8-fluoro-4-methyl-3-oxo-3,4-dihydro-2h-benzo[1,4]oxazin-6-yl)-2-hydroxy-1-methyl-propyl]-biphenyl-3-yloxy}-acetic acid ethyl ester

Procedure

In analogy to Example 1, step 5, 6-[2-(3-chloro-4′-fluoro-3′-hydroxy-biphenyl-4-yl)-1-hydroxy-1-trifluoromethyl-propyl]-8-fluoro-4-methyl-4H-benzo[1,4]oxazin-3-one was reacted with ethylbromoacetate and cesium carbonate to give the title compound as a colorless foam. MS (m/e)=614.2 [M+H+].

Sources & evidence

ORD record: ord-81abb77d1b1f4b2bad5dde30dd730bb6
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268820B2

Linked notes

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