(2S)-2-(((tert-butoxy)carbonyl)amino)-4-phenylbutanoic acid → HCID 131722642, compound

HRID 1067067Notes

Reaction equation

HRID 1067067 reaction equation
[C:1]([NH:8][C@H:9]([C:18]([OH:20])=O)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[F:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][NH:30][C:31](=[O:46])[C@H:32]([CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[NH:33][CH3:34])=[CH:24][CH:23]=1>>[F:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][NH:30][C:31](=[O:46])[C@H:32]([CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][C:42]([CH3:44])([CH3:43])[CH3:45])=[O:40])[N:33]([C:18](=[O:20])[C@H:9]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH3:34])=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 7018726(2S)-2-(((tert-butoxy)carbonyl)amino)-4-phenylbutanoic acidHCID 131722643HCID 131722643, compound

Product 1

HCID 131722642HCID 131722642, compound

Procedure

Using Procedure D, Boc-homophenylalanine (143 mg) and Nδ-Boc-Nα-methylornithine 2-(4-fluorophenyl)ethylamide (B) (crude product) gave desired compound (195 mg) as a glassy solid which was purified by flash chromatography: 1H NMR (400 MHz, CDCl3) δ1.52 (2 s, 18H).1.71 (m, 2H), 1.82 (m, 4H), 2.62-2.80 (m, 7H), 3.12 (m, 2H), 3.45 (m, 2H), 4.61 (m, 1H), 4.92 (m, 1H), 6.89 (m, 2H), 7.13 (m, 2H), 7.20 (m, 3H), and 7.32 (m, 2H).

Sources & evidence

ORD record
ord-fcfccb272cb14707bb327f5fde2640d6
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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