Methyl 4-bromo-alpha-hydroxybenzeneacetate → (4'-{[2-(tert-Butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-1,1'-biphenyl-4-yl)(hydroxy)acetic acid

HRID 2076665Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:13])[C:9]([O:11]C)=[O:10])=[CH:4][CH:3]=1.[OH:14][C:15]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[C:24]([CH2:32][O:33][C:34]2[CH:39]=[CH:38][C:37](B3OC(C)(C)C(C)(C)O3)=[CH:36][CH:35]=2)[C:16]=1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>>[C:20]([O:19][C:17]([C:16]1[C:15]([OH:14])=[C:27]([C:28]([F:29])([F:30])[F:31])[CH:26]=[CH:25][C:24]=1[CH2:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([C:2]2[CH:7]=[CH:6][C:5]([CH:8]([OH:13])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=2)=[CH:36][CH:35]=1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

Reactant 2

HCID 14571696Methyl 4-bromo-alpha-hydroxybenzeneacetate

HCID 67119153Tert-butyl 2-hydroxy-6-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methyl}-3-(trifluoromethyl)benzoate

Product 1

HCID 67119069(4'-{[2-(tert-Butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-1,1'-biphenyl-4-yl)(hydroxy)acetic acid

Procedure

According to a method similar to Example (31) and Example (17-4), from methyl (4-bromophenyl)(hydroxy)acetate (100 mg, 0.41 mmol) and tert-butyl 2-hydroxy-6-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methyl}-3-(trifluoromethyl)benzoate (170 mg, 0.34 mmol) obtained in Example (22-4), the title compound was obtained as a grayish white powder (14 mg, yield: 8%).

Sources & evidence

ORD record: ord-b051f573660d425093019e0a6009414e
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923573B2

Reaction notes

Loading…