Phenylboronic Acid → HCID 86617218, compound

HRID 1926679Notes

Reaction equation

HRID 1926679 reaction equation
[CH3:1][C@@H:2]1[CH2:7][N:6]([C@@H:8]([C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4][N:3]1[CH2:22][C:23]([O-:25])=[O:24].C1(B(O)O)C=CC=CC=1.[CH3:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1B(O)O.[CH3:45][C:46]1[CH:47]=[C:48](B(O)O)[CH:49]=[CH:50][CH:51]=1.[CH3:55][C:56]1[CH:61]=CC(B(O)O)=C[CH:57]=1>>[CH3:1][C@@H:2]1[CH2:7][N:6]([C@@H:8]([C:15]2[CH:20]=[CH:19][C:18]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=3[CH3:35])=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4][N:3]1[CH2:22][C:23]([O:25][C:46]([CH3:47])([CH3:51])[CH3:45])=[O:24].[CH3:1][C@@H:2]1[CH2:7][N:6]([C@@H:8]([C:15]2[CH:20]=[CH:19][C:18]([C:50]3[CH:49]=[CH:48][CH:47]=[C:46]([CH3:45])[CH:51]=3)=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4][N:3]1[CH2:22][C:23]([O:25][C:56]([CH3:61])([CH3:57])[CH3:55])=[O:24]

Participants

7

Reactant 5

HCID 66827Phenylboronic AcidHCID 79799Tolylboronic acidHCID 27332672-Methylphenyl boronic acidHCID 27339503-Tolylboronic acidHCID 86617221HCID 86617221, compound

Product 2

HCID 86617218HCID 86617218, compoundHCID 86617219HCID 86617219, compound

Procedure

Proceeding as described in Example 6 above, but substituting tert-butyl 2-(4-(3 -bromophenyl)(phenyl)methyl)piperazin-1-Aacetate with 2-((R)-2-methyl-4-((R)-(4-bromophenyl)(phenyl)methyl)piperazin-1-yl)acetate and treating it with phenylboronic acid, 2-methylphenylboronic acid, 3-methylphenylboronic acid and 4-methylphenylboronic acid provided tert-butyl ((R)-2-methyl-4-((R)-(4-biphenyl)(phenyl)methyl)-piperazin-1-yl)acetate, tert-butyl ((R)-2-methyl-4-((R)-(4-(2-methylphenyl)phenyl)(phenyl)methyl)-piperazin-1-yl )acetate, tert butyl ((R)-2-methyl-4-((R)-(4-(3-methylphenyl)phenyl)-(phenyl)methyl)-piperazin-1-yl)acetate, and tert-butyl ((R)-2-methyl-44-((R)-(4-(4-methylphenyl)phenyl)- (phenyl)methyl)-piperazin-1-yl)acetate respectively, which were converted to [(R)-4-((R)-biphenyl-4-yl-phenyl-methyl)-2-methyl-piperazin-l-yl]-acetic acid; [(R)-2-methyl-4-[(R)-(2′-methyl-biphenyl-4-yl)-phenyl-methyl]-piperazin-l-yl]-acetic acid; [(R)-2-methyl-4-[(R)-(3′- methyl-biphenyl-4-yl)-phenyl-methyl]-piperazin-l-yl]-acetic acid; and [(R)-2-methyl-4-[(R)-(4′- methyl-biphenyl-4-yl)-phenyl-methyl]-piperazin-1-yl]-acetic acid, respectively, as described in Example 4 above.

Sources & evidence

ORD record
ord-18c0eb06908643049ca0ebab4a6925f7
Source dataset
uspto-grants-2012_05
Patent number
US08183244B2

Reaction notes

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