HCID 58979648, compound → [1-(2,6-Difluorobenzyl)cyclobutyl]methyl(1S)-5-{[(methylamino)carbonyl]amino}-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate
Reaction equation
[OH:1][CH:2]([C@@H:14]([NH:24][C:25](=[O:41])[O:26][CH2:27][C:28]1([CH2:32][C:33]2[C:38]([F:39])=[CH:37][CH:36]=[CH:35][C:34]=2[F:40])[CH2:31][CH2:30][CH2:29]1)[CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([NH:22][CH3:23])=[O:21])[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)CCCCC1)CCCCNC(N1CCOCC1)=O)C(=O)N[C@@H](C1C=CC=CC=1)C>>[CH3:23][NH:22][C:20]([NH:19][CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]([NH:24][C:25](=[O:41])[O:26][CH2:27][C:28]1([CH2:32][C:33]2[C:34]([F:40])=[CH:35][CH:36]=[CH:37][C:38]=2[F:39])[CH2:29][CH2:30][CH2:31]1)[C:2](=[O:1])[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])=[O:21]Participants
Reactant 2
Product 1
Procedure
[1-(2,6-Difluorobenzyl)cyclobutyl]methyl(1S)-5-{[(methylamino)carbonyl]amino}-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate was prepared as in example 9j except that [1-(2,6-difluorobenzyl)cyclobutyl]methyl(1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)-5-{[(methylamino)carbonyl]amino}pentylcarbamate was substituted for (1-benzylcyclohexyl)methyl(1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)-5-[(4-morpholinylcarbonyl)amino]pentylcarbamate. 1H NMR (300 MHz, DMSO-d6) δ 9.19 (m, 1H), 7.58 (m, 1H), 7.05-7.43 (m, 8H), 5.86 (m, 1H), 5.65 (m, 1H), 4.98 (m, 1H), 4.76 (m, 1H), 3.95 (m, 2H). 3.25 under water peak (m, 3H), 2.96 (m, 2H), 2.78 (s, 2H), 1.60-1.90 (m, 6H), 1.25-1.50 (m, 9H). ES-LCMS m/z 571 (M−H).
Sources & evidence
- ORD record
- ord-15b3550ffc8d4c898477f35ce8aef3d8
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07282512B2
Reaction notes
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