(2S)-2-(((tert-butoxy)carbonyl)amino)-4-phenylbutanoic acid → HCID 131722646, compound

HRID 1067071Notes

Reaction equation

HRID 1067071 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].[CH3:21][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>>[CH3:21][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]([CH3:44])([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:24][CH:23]=1

Participants

3

Reactant 2

HCID 7018726(2S)-2-(((tert-butoxy)carbonyl)amino)-4-phenylbutanoic acidHCID 131722647HCID 131722647, compound

Product 1

HCID 131722646HCID 131722646, compound

Procedure

Using Procedure D, Boc-homophenylalanine (143 mg) and Nδ-Boc-Nα-methylornithine 2-(4-methylphenyl)ethylamide (crude product from B) afforded titled product (195 mg) as a glassy solid after silica gel chromatography: 1H NMR (400 MHz, CDCl3) δ1.44 (2 s, 18H), 1.63 (m, 2H), 1.83 (m, 2H, 2.33 s, 3H), 2.63-279 (m, 7H), 3.09 (m, 2H), 3.45 (m, 2H), 4.51 (m, 1H), 4.98 (m, 1H), 7.09 (m, 4H) (m, 3H), and 7.31 (m, 2H).

Sources & evidence

ORD record
ord-4e64e54b09fe480eb4720e23a878b142
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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