HCID 7015801, compound → HCID 22961348, compound

HRID 2304865Notes

Reaction equation

HRID 2304865 reaction equation
[O: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[O: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 53866134(1r)-1-[(Rs)-(2-benzoxazolyl)hydroxymethyl]-3-phenylpropylamine

Product 1

HCID 22961348HCID 22961348, compoundYield 240.3%

Procedure

(1R)-1-[(RS)-(2-benzoxazolyl)hydroxymethyl]-3-phenylpropylamine (62 mg) is coupled with N,N′-bis-Boc-D-ornithine (51 mg) to afford the title compound (110 mg) as a glassy solid: 1H NMR (400 MHz, CDCl3, 3:2 mixture of diastereomers) δ 1.39-1.42 (2s, 18H), 1.58 (m, 3H), 1.86 (m, 2H), 2.09 (m, 1H), 2.67-2.78 (m, 1.6H), 2.92 (m, 0.4H), 2.96-3.22 (m, 2H), 4.07 (m, 0.4H), 4.18 (m, 0.6H), 4.59 (m, 1.4H), 4.78 (m, 0.6H), 5.04 (s, 1H), 5.14 (bd, 0.4H, NH), 5.26 (bd, 0.6H, NH), 7.09-7.37 (m, 7H), 7.50 (m, 1H), and 7.71 (m, 1H).

Sources & evidence

ORD record
ord-723e4b1ce7cb41659835be3fe798e971
Source dataset
uspto-grants-2002_08
Patent number
US06436980B1

Reaction notes

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