Potassium Bromide → HCID 46181432, compound

HRID 75784Notes

Reaction equation

C[O:2][C:3](=[O:33])[C@@H:4]([NH:9][C:10]([C:12]1[O:16][N:15]=[C:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:25])=[CH:19][CH:18]=2)[CH:13]=1)=[O:11])[CH2:5][CH:6]([CH3:8])[CH3:7].[K+].[Br-]>>[CH:27]1([NH:26][C:24](=[O:25])[NH:23][C:20]2[CH:21]=[CH:22][C:17]([C:14]3[CH:13]=[C:12]([C:10]([NH:9][C@@H:4]([CH2:5][CH:6]([CH3:7])[CH3:8])[C:3]([OH:33])=[O:2])=[O:11])[O:16][N:15]=3)=[CH:18][CH:19]=2)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

Reactant 2

HCID 253877Potassium Bromide

HCID 46181431(S)-2-({3-[4-(3-cyclohexyl-ureido)-phenyl]-isoxazole-5-carbonyl}-amino)-4-methyl-pentanoic acid methyl ester

Product 1

HCID 46181432HCID 46181432, compoundYield 70.7%

Procedure

The title compound was prepared from (S)-2-({3-[4-(3-cyclohexyl-ureido)-phenyl]-isoxazole-5-carbonyl}-amino)-4-methyl-pentanoic acid methyl ester as set forth in Example 8 and was obtained in 70.7% yield. Mass (ES+): 443 (M++1); IR (KBr): 3326, 3305, 2935, 1748, 1635 (br), 1544, 1529; 1H NMR (DMSO-d6) δ: 0.87, 0.91 (2×d, 6H), 1.09-1.81 (5×m, 13H), 3.45 (br, 1H), 4.38 (m, 1H), 6.16 (d, 1H), 7.50 (d, 2H), 7.56 (s, 1H), 7.75 (d, 2H), 8.58 (s, 1H), 9.14 (d, 1H), 12.76 (br, 1H).

Workup

customwas obtained in 70.7% yield

Sources & evidence

ORD record: ord-61fbb88977ca47aaacdb5d198f5f4552
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835428B2

Reaction notes

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