(1-benzylcyclopentyl)methyl(1S)-1-(1-hydroxy-2-oxo-2-{[(1r)-1-phenylethyl]amino}ethyl)pentylcarbamate → (1-benzylcyclopentyl)methyl(1S)-1-(oxo{[(1r)-1-phenylethyl]amino}acetyl)pentylcarbamate
Reaction equation
[OH:1][CH:2]([C@@H:14]([NH:19][C:20](=[O:35])[O:21][CH2:22][C:23]1([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1)[CH2:15][CH2:16][CH2:17][CH3:18])[C:3](=[O:13])[NH:4][C@@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6].OC([C@@H](NC(=O)OCC1(CC2C=CC=CC=2)CCC1)CCCC)C(=O)N[C@@H](C1C=CC=CC=1)C>>[O:13]=[C:3]([NH:4][C@@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6])[C:2]([C@@H:14]([NH:19][C:20](=[O:35])[O:21][CH2:22][C:23]1([CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:24][CH2:25][CH2:26][CH2:27]1)[CH2:15][CH2:16][CH2:17][CH3:18])=[O:1]Participants
3
Reactant 2
Product 1
Procedure
(1-Benzylcyclopentyl)methyl(1S)-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate was prepared as in example 6c except that (1-benzylcyclopentyl)methyl(1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamate was substituted for (1-benzylcyclobutyl)methyl(1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamate. M.P.=108-110° C. Elemental analysis: Theory; C=72.77%, H=8.00%, N=5.85%. Found; C=72.62%, H=8.00%, N=5.84%. 1H NMR (300 MHz, 80° C., DMSO-d6) δ 8.82 (d, J=8 Hz, 1H), 7.19-7.39 (m, 11H), 5.02 (qnt, J=7 Hz, 1H), 4.86 (m, 1H), 3.69 (d, J=3 Hz, 2H), 2.69 (s, 2H), 1.20-1.65 (m, 17H), 0.87 (t, J=7 Hz, 3H). ES-LCMS m/z 501 (M+Na). HRMS C29H38N2O4 m/z 501.2729 (M+Na)Cal; 501.2731 (M+Na)Obs.
Sources & evidence
- ORD record
- ord-3c7142fbba6d4f0e9228c1a20060be8c
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07282512B2
Reaction notes
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