HCID 7015801, compound → n,n'-Bis-boc-(2r)-2,5-diamino-n-[(1r)-1-[(rs)-(2-benzimidazolyl)hydroxymethyl]-3-phenylpropyl]valeramide

HRID 2304870Notes

Reaction equation

HRID 2304870 reaction equation
[C:1]([NH:11][C@@H:12]([CH:21]([C:23]1[NH:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=1)[OH:22])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([O:3]CC1C=CC=CC=1)=[O:2].C([NH:39][C@@H:40]([C:52]([OH:54])=O)[CH2:41][CH2:42][CH2:43][NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])(OC(C)(C)C)=O>FC(F)(F)C(O)=O>[C:1]([N:11]([C@@H:12]([CH:21]([C:23]1[NH:27][C:26]2[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=2[N:24]=1)[OH:22])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:52](=[O:54])[C@H:40]([NH2:39])[CH2:41][CH2:42][CH2:43][NH:44][C:45]([O:47][C:48]([CH3:49])([CH3:50])[CH3:51])=[O:46])([O:3][C:15]([CH3:20])([CH3:16])[CH3:14])=[O:2]

Participants

4

Reactant 2

HCID 7015801HCID 7015801, compoundHCID 22961338n-Cbz-(1r)-1-[(rs)-(2-benzimidazolyl)hydroxymethyl]-3-phenylpropylamine

Product 1

HCID 22961346n,n'-Bis-boc-(2r)-2,5-diamino-n-[(1r)-1-[(rs)-(2-benzimidazolyl)hydroxymethyl]-3-phenylpropyl]valeramide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N-Cbz-(1R)-1-[(RS)-(2-Benzimidazolyl)hydroxymethyl]-3-phenylpropylamine (581 mg) is deprotected in trifluoroacetic acid, and the residue is coupled to N,N′-bis-Boc-D-ornithine to afford the title compound (110 mg): mass spectrum (ES+) m/e 596.3 (M+1); 1H NMR (400 MHz, CDCl3, 3:2 mixture of diastereomers) δ 1.46 (m, 9H), 1.42 (s, 9H), 1.58 (m, 4H), 2.02 (m, 2H), 2.63 (m, 2H), 2.82 (m, 2H), 3.18 (m, 1H), 4.16 (m, 1H), 4.49 (m, 1H), 5.17 (m, 1H), 5.42 (m, 1H), 7.03-7.23 (m, 8H), and 7.57 (m, 1H).

Sources & evidence

ORD record
ord-7c5999e2a7cc452faad77390a6e2c4fa
Source dataset
uspto-grants-2002_08
Patent number
US06436980B1

Reaction notes

Loading…