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

HRID 1532787Notes

Reaction equation

HRID 1532787 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([OH:21])[C@H:11]([NH2:20])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([NH:29][C@@H:30]([C:42](O)=[O:43])[CH2:31][CH2:32][CH2:33][NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])(OC(C)(C)C)=O>>[C:35]([N:20]([C@@H:11]([CH:10]([C:2]1[S:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1)[OH:21])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:42](=[O:43])[C@H:30]([NH2:29])[CH2:31][CH2:32][CH2:33][NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]

Participants

3

Reactant 2

HCID 7015801HCID 7015801, compoundHCID 70177074(1R)-1-[(RS)-(2-Benzothiazolyl)hydroxymethyl]-3-phenylpropylamine

Product 1

HCID 22961347n,n'-Bis-boc-(2r)-2,5-diamino-n-[(1r)-1-[(rs)-(2-benzothiazolyl)hydroxymethyl]-3-phenylpropyl]valeramide

Procedure

(1R)-1-[(RS)-(2-Benzothiazolyl)hydroxymethyl]-3-phenylpropylamine (72 mg) was coupled to N,N′-bis-Boc-D-ornithine to afford the title compound (11 mg) as a glassy solid: 1H NMR (400 MHz, CDCl3, 3:2 mixture of diastereomers) δ1.41 (s, 9H), 1.44 (s, 9H), 1.60 (m, 2H ), 1.19 (m, 4H), 2.20 (m, 2H), 2.72-2.91 (m, 2H), 4.11 (m, 1H), 4.31 (m, 0.4H), 4.41 (m, 0.6H), 5.06 (m, 0.6H), 5.19 (d, J=1.1 Hz, 0.4), 7.20 (m, 3H), 7.26 (m, 2H), 7.40 (t, J=8.5 Hz, 1H), 7.49 (t, J=9.3 Hz, 1H), 7.87 (d, J=8.3 Hz, 1H ), and 7.98 (d, J=9.4 Hz, 1H).

Sources & evidence

ORD record
ord-e16e378397c54b9fbc61aad040059791
Source dataset
uspto-grants-2001_03
Patent number
US06204279B1

Reaction notes

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