HCID 7015801, compound → N,N'-Bis-Boc-(2R)-2,5-Diamino-N-[(1R)-1-[(RS)-(5,6-dimethyl-2-benzoxazolyl)hydroxymethyl]-3-phenylpropyl]valeramide

HRID 2304868Notes

Reaction equation

HRID 2304868 reaction equation
[CH3:1][C:2]1[C:3]([CH3:23])=[CH:4][C:5]2[O:9][C:8]([CH:10]([OH:21])[C@H:11]([NH2:20])[CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:7][C:6]=2[CH:22]=1.C([NH:31][C@@H:32]([C:44](O)=[O:45])[CH2:33][CH2:34][CH2:35][NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])(OC(C)(C)C)=O>>[C:37]([N:20]([C@@H:11]([CH:10]([C:8]1[O:9][C:5]2[CH:4]=[C:3]([CH3:23])[C:2]([CH3:1])=[CH:22][C:6]=2[N:7]=1)[OH:21])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:44](=[O:45])[C@H:32]([NH2:31])[CH2:33][CH2:34][CH2:35][NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38]

Participants

3

Reactant 2

HCID 7015801HCID 7015801, compoundHCID 53812656(1r)-1-[(Rs)-(5,6-dimethyl-2-benzoxazolyl)hydroxymethyl]-3-phenylpropylamine

Product 1

HCID 22961349N,N'-Bis-Boc-(2R)-2,5-Diamino-N-[(1R)-1-[(RS)-(5,6-dimethyl-2-benzoxazolyl)hydroxymethyl]-3-phenylpropyl]valeramide

Procedure

(1R)-1-[(RS)-(5,6-dimethyl-2-benzoxazolyl)hydroxymethyl]-3-phenylpropylamine (157 mg) is coupled with N,N′-bis-Boc-D-ornithine to afford the title compound (343 mg) as a white solid: 1H NMR (400 MHz, CDCl3, 3:2 mixture of diastereomers) δ 1.39-1.43 (bd, 19H), 1.43-1.64 (m, 4H), 1.83 (m, 1H), 2.38 (m, 6H), 2.61-3.21 (m, 4H), 4.08 (m, 1H), 4.59 (m, 1H), 5.02 (s, 1H), 5.18 (bd, 0.6H, NH), 5.28 (bd, 0.4H, NH), 7.12-7.35 (m, 6H), 7.41 (s, 0.4H), and 7.46 (s, 0.6H).

Sources & evidence

ORD record
ord-46b538d107484e7f8923a6d52cfc9b65
Source dataset
uspto-grants-2002_08
Patent number
US06436980B1

Reaction notes

Loading…