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

HRID 2304869Notes

Reaction equation

HRID 2304869 reaction equation
[Cl:1][C:2]1[CH:3]=[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:30][C@@H:31]([C:43](O)=[O:44])[CH2:32][CH2:33][CH2:34][NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])(OC(C)(C)C)=O>>[C:36]([N:20]([C@@H:11]([CH:10]([C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:22][C:6]=2[N:7]=1)[OH:21])[CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:43](=[O:44])[C@H:31]([NH2:30])[CH2:32][CH2:33][CH2:34][NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37]

Participants

3

Reactant 2

HCID 7015801HCID 7015801, compoundHCID 53701314(1r)-1-[(Rs)-(5-chloro-2-benzoxazolyl)hydroxymethyl]-3-phenylpropylamine

Product 1

HCID 22961350N,N'-Bis-Boc-(2R)-2,5-Diamino-N-[(1R)-1-[(RS)-(5-chloro-2-benzoxazolyl)hydroxymethyl]-3-phenylpropyl]valeramide

Procedure

(1R)-1-[(RS)-(5-Chloro-2-benzoxazolyl)hydroxymethyl]-3-phenylpropylamine (136 mg) was coupled with N,N′-bis-Boc-D-ornithine to afford the title compound (150 mg) as a glassy solid: mass spectrum (ES+) m/e 35Cl 653.4, 37Cl 655.4 (M+23 (Na)); 1H NMR (400 MHz, CDCl3, 7:3 mixture of diastereomers) δ 1.40 (m, 18H), 1.62 (m, 4H), 1.90 (m, 2H), 2.74 (m, 2H), 3.03-3.23 (m, 2H), 4.09 (m, 0.3H), 4.19 (m, 0.7H), 4.58 (m, 0.7H), 4.69 (m, 0,3H), 5.03 (m, 0.7H), 5.20 (m, 0.3H), 7.11-7.23 (m, 6H), 7.37 (m, 2H), 7.53 (m, 1H), 7.68 (m, 0.3H), and 7.76 (m, 0.7H).

Sources & evidence

ORD record
ord-3b0f2edd7a7f487ebc1224fb01cc1a77
Source dataset
uspto-grants-2002_08
Patent number
US06436980B1

Reaction notes

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