HCID 70057716, compound → 2,5-Di-{N-[(Imidazol-2-yl)-thiomethylcarbonyl]-(L)-Valyl}amino-3,4-dihydroxy-1,6-diphenyl hexane

HRID 52836Notes

Reaction equation

Br[CH2:2][C:3]([NH:5][C@H:6]([C:10]([NH:12][CH:13]([CH:21]([OH:44])[CH:22]([OH:43])[CH:23]([NH:31][C:32](=[O:42])[C@H:33]([CH:39]([CH3:41])[CH3:40])[NH:34][C:35](=[O:38])[CH2:36]Br)[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11])[CH:7]([CH3:9])[CH3:8])=[O:4].[SH:45][C:46]1[NH:47][CH:48]=[CH:49][N:50]=1>>[NH:47]1[CH:48]=[CH:49][N:50]=[C:46]1[S:45][CH2:2][C:3]([NH:5][C@H:6]([C:10]([NH:12][CH:13]([CH:21]([OH:44])[CH:22]([OH:43])[CH:23]([NH:31][C:32](=[O:42])[C@H:33]([CH:39]([CH3:41])[CH3:40])[NH:34][C:35]([CH2:36][S:45][C:46]1[NH:47][CH:48]=[CH:49][N:50]=1)=[O:38])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11])[CH:7]([CH3:9])[CH3:8])=[O:4]

Participants

Reactant 2

HCID 70057716HCID 70057716, compound

HCID 178527877HCID 178527877, compound

Product 1

HCID 701302772,5-Di-{N-[(Imidazol-2-yl)-thiomethylcarbonyl]-(L)-Valyl}amino-3,4-dihydroxy-1,6-diphenyl hexaneYield 47.5%

Procedure

The resultant compound of Example 251 (150 mg, 0.2 mmol) was reacted with 2-mercaptoimidazole (40.6 mg) by the procedure described in Example 252 and similarly purified to afford the title compound (74 mg, 47%). 1H NMR (DMSO-d6, 300 MHz) δ 0.63 (m, 12H), 1.84 (m, 2H), 2.25-2.80 (m, 4H), 3.05-3.82 (m, 12H), 4.44 (m, 2H), 7.14 (m, 14H), 7.48 (bd, 2H), 8.07 (bd, 2H). MS (FAB) m/e 779 (M+H)+.

Workup

customsimilarly purified

Sources & evidence

ORD record: ord-edd996bb594048adbf6145cfa7f2e7cb
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05616714

Reaction notes

Loading…