beta-Phenylisovaleric acid → HCID 70976040, compound

HRID 535610Notes

Reaction equation

[NH2:1][N:2]1[N:11]=[C:10]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:21].[CH3:22][C:23]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH3:28])[CH2:24][C:25](O)=[O:26]>>[CH3:28][C:23]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH3:22])[CH2:24][C:25]([NH:1][N:2]1[N:11]=[C:10]([S:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)(=[O:14])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:21])=[O:26]

Participants

Reactant 2

HCID 13890beta-Phenylisovaleric acid

HCID 70975871HCID 70975871, compound

Product 1

HCID 70976040HCID 70976040, compound

Procedure

The product from Example 68B and 3-methyl-3-phenylbutanoic acid were processed using a method similar to that described in Example 10C to afford the title compound. 1H NMR (500 MHz, DMSO-d6) δ 11.45 (s, 1H), 8.56 (d, J=8.2, 1H), 8.41-8.34 (m, 1H), 8.14-8.08 (m, 1H), 8.04-7.96 (m, 3H), 7.84-7.77 (m, 1H), 7.68 (dd, J=10.8, 5.0, 2H), 7.38 (dd, J=8.4, 1.1, 2H), 7.33-7.27 (m, 2H), 7.20-7.14 (m, 1H), 2.54 (s, 2H), 1.32 (s, 6H); MS (DCI+) M/Z 479 (M+NH4)+.

Sources & evidence

ORD record: ord-ee8fe51dd92149cb9b4ec465f681b77a
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859549B2

Reaction notes

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