[5-(4-Bromo-3-methyl-phenyl)-3-methyl-isoxazol-4-yl]carbamic acid (R)-1-(2-fluoro-phenyl)-ethyl Ester → 2-(4'-{4-[(R)-1-(2-fluoro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-2'-methyl-biphenyl-4-yl)-propionic acid ethyl ester

HRID 553716Notes

Reaction equation

HRID 553716 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([O:10][C:11](=[O:27])[NH:12][C:13]1[C:14]([CH3:26])=[N:15][O:16][C:17]=1[C:18]1[CH:23]=[CH:22][C:21](Br)=[C:20]([CH3:25])[CH:19]=1)[CH3:9].[CH2:28]([O:30][C:31](=[O:49])[CH:32]([C:34]1[CH:39]=[CH:38][C:37](B2OC(C)(C)C(C)(C)O2)=[CH:36][CH:35]=1)[CH3:33])[CH3:29]>>[CH2:28]([O:30][C:31](=[O:49])[CH:32]([C:34]1[CH:39]=[CH:38][C:37]([C:21]2[CH:22]=[CH:23][C:18]([C:17]3[O:16][N:15]=[C:14]([CH3:26])[C:13]=3[NH:12][C:11]([O:10][C@@H:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[CH3:9])=[O:27])=[CH:19][C:20]=2[CH3:25])=[CH:36][CH:35]=1)[CH3:33])[CH3:29]

Participants

3

Reactant 2

HCID 54765945[5-(4-Bromo-3-methyl-phenyl)-3-methyl-isoxazol-4-yl]carbamic acid (R)-1-(2-fluoro-phenyl)-ethyl EsterHCID 58539349Ethyl 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate

Product 1

HCID 673526282-(4'-{4-[(R)-1-(2-fluoro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-2'-methyl-biphenyl-4-yl)-propionic acid ethyl ester

Procedure

Following the procedure described in Example 36, Step 6, [5-(4-bromo-3-methyl-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid (R)-1-(2-fluoro-phenyl)-ethyl ester and 2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid ethyl ester were reacted to provide 2-(4′-{4-[(R)-1-(2-fluoro-phenyl)-ethoxycarbonylamino]-3-methyl-isoxazol-5-yl}-2′-methyl-biphenyl-4-yl)-propionic acid ethyl ester, which was hydrolyzed to the acid as described in Example 36, Step 7.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-dfbe82311d724115897d9fdfd1586820
Source dataset
uspto-grants-2011_11
Patent number
US08048902B2

Reaction notes

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