Ethyl 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)acetate → {4'-[3-Methyl-4-((R)-1-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-biphenyl-2-yl}-acetic acid ethyl ester

HRID 2092473Notes

Reaction equation

HRID 2092473 reaction equation
[C:1]1([C@H:7]([O:9][C:10](=[O:25])[NH:11][C:12]2[C:13]([CH3:24])=[N:14][O:15][C:16]=2[C:17]2[CH:22]=[CH:21][C:20](Br)=[CH:19][CH:18]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:26]([O:28][C:29](=[O:46])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1B1OC(C)(C)C(C)(C)O1)[CH3:27]>>[CH2:26]([O:28][C:29](=[O:46])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:20]1[CH:21]=[CH:22][C:17]([C:16]2[O:15][N:14]=[C:13]([CH3:24])[C:12]=2[NH:11][C:10]([O:9][C@@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:8])=[O:25])=[CH:18][CH:19]=1)[CH3:27]

Participants

3

Reactant 2

HCID 58539376Ethyl 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)acetateHCID 66660383(1R)-1-Phenylethyl N-(5-(4-bromophenyl)-3-methyl-4-isoxazolyl)carbamate

Product 1

HCID 70875876{4'-[3-Methyl-4-((R)-1-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-biphenyl-2-yl}-acetic acid ethyl ester

Procedure

Following the procedure described in Example 36, Step 6, [5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-carbamic acid (R)-1-phenyl-ethyl ester and [2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl ester were reacted to provide {4′-[3-Methyl-4-((R)-1-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-biphenyl-2-yl}-acetic ac id ethyl ester, which was hydrolyzed to the acid as described in Example 34, Step 2.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-78f4bb2ac451460bbbe80edd70bdbdef
Source dataset
uspto-grants-2013_05
Patent number
US08440707B2

Reaction notes

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