(1-benzylcyclohexyl)methyl(1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)-5-[(4-morpholinylcarbonyl)amino]pentylcarbamate → [1-(4-Pyridinylmethyl)cyclobutyl]methyl(1S)-5-[(4-morpholinylcarbonyl)amino]-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate

HRID 1180751Notes

Reaction equation

HRID 1180751 reaction equation
[OH:1][CH:2]([C@@H:14]([NH:28][C:29](=[O:43])[O:30][CH2:31][C:32]1([CH2:36][C:37]2[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=2)[CH2:35][CH2:34][CH2:33]1)[CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=[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>>[N:22]1([C:20]([NH:19][CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]([NH:28][C:29](=[O:43])[O:30][CH2:31][C:32]2([CH2:36][C:37]3[CH:38]=[CH:39][N:40]=[CH:41][CH:42]=3)[CH2:35][CH2:34][CH2:33]2)[C:2](=[O:1])[C:3](=[O:13])[NH:4][C@@H:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:6])=[O:21])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 58979648(1-benzylcyclohexyl)methyl(1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)-5-[(4-morpholinylcarbonyl)amino]pentylcarbamateHCID 58979650[1-(4-pyridinylmethyl)cyclobutyl]methyl(1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)-5-[(4-morpholinylcarbonyl)amino]pentylcarbamate

Product 1

HCID 44394384[1-(4-Pyridinylmethyl)cyclobutyl]methyl(1S)-5-[(4-morpholinylcarbonyl)amino]-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate

Procedure

[1-(4-Pyridinylmethyl)cyclobutyl]methyl(1S)-5-[(4-morpholinylcarbonyl)amino]-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate was prepared as in example 9j except that [1-(4-pyridinylmethyl)cyclobutyl]methyl(1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)-5-[(4-morpholinylcarbonyl)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, 80° C., DMSO-d6) δ 8.92 (m, 1 H), 8.49 (m, 2H), 7.20-7.36 (m, 8H), 6.31 (m, 1H), 5.01 (qnt, J=7 Hz, 1H), 4.82 (m, 1H), 3.78 (s, 2H), 3.53 (t, J=5 Hz, 4H), 3.24 (t, J=5 Hz, 4H), 3.01 (m, 2H), 2.80 (s, 2H), 1.83-1.90 (m, 6H), 1.42-1.48 (m, 9H). ES-LCMS m/z 594 (M+H). HRMS C32H43N5O6 m/z 594.3291 (M+H)Cal; 594.3279 (M+Na)Obs.

Sources & evidence

ORD record
ord-bf957fcf6f734753b9f63fa8a4bc99a7
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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