(1-benzylcyclohexyl)methyl(1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)-5-[(4-morpholinylcarbonyl)amino]pentylcarbamate → [1-(3-Pyridinylmethyl)cyclobutyl]methyl(1S)-5-[(4-morpholinylcarbonyl)amino]-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate

HRID 1180752Notes

Reaction equation

HRID 1180752 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:38]=[N:39][CH:40]=[CH:41][CH:42]=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]=[N:39][CH: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 58979669[1-(3-pyridinylmethyl)cyclobutyl]methyl(1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)-5-[(4-morpholinylcarbonyl)amino]pentylcarbamate

Product 1

HCID 58979656[1-(3-Pyridinylmethyl)cyclobutyl]methyl(1S)-5-[(4-morpholinylcarbonyl)amino]-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate

Procedure

[1-(3-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-(3-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. ES-LCMS m/z 616 (M+Na). Retention time=2.94 min. LC-MS results obtained using a Phenomenex max RP 50×2 MM column with 4 u packing eluted at 0.8 mL/min with a 5 minute gradient from 85% water: 15% methanol to 100% methanol. The mobile phase contained a 0.1% formic acid modifier. HRMS C32H43N5O6 m/z 594.3292 (M+Na)Cal; 594.3279 (M+Na)Obs.

Workup

  1. customLC-MS results
  2. customobtained
  3. washeluted at 0.8 mL/min with a 5 minute gradient from 85% water

Sources & evidence

ORD record
ord-e04bc86f290b45d9afa9c5092041a2cc
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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