HCID 58979652, compound → HCID 10174359, compound

HRID 1180739Notes

Reaction equation

[OH:1][CH:2]([C@@H:14]([NH:19][C:20](=[O:36])[O:21][CH2:22][C:23]1([CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[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(CCC2C=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:36])[O:21][CH2:22][C:23]1([CH2:27][CH2:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:24][CH2:25][CH2:26]1)[CH2:15][CH2:16][CH2:17][CH3:18])=[O:1]

Participants

Reactant 2

HCID 58979652HCID 58979652, compound

HCID 58979693HCID 58979693, compound

Product 1

HCID 10174359HCID 10174359, compound

Procedure

[1-(3-phenylpropyl)cyclobutyl]methyl(1S)-1-(oxo{[(1R)-1-phenylethyl]amino}acetyl)pentylcarbamate was prepared as in example 6c except that [1-(3-phenylpropyl)cyclobutyl]methyl(1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamate was substituted for [1-(2-phenylethyl)cyclobutyl]methyl(1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamate. M.P.=91-93° C. Elemental analysis: Theory; C=73.14%, H=8.18%, N=5.69%. Found; C=72.81%, H=8.22%, N=5.82%. 1H NMR (400 MHz, DMSO-d6) δ 9.10 (d, J=8 Hz, 1H), 7.45 (d, J=8 Hz, 1H), 7.11-7.26 (m, 10H), 4.91 (qnt, J=8 Hz, 1H), 4.70 (m, 1H), 3.85 (s, 2H), 2.50 (m, 2H), 1.55-1.74 (m, 6H), 1.13-1.45 (m, 13H), 0.74 (t, J=7 Hz, 13H). ES-LCMS m/z 515 (M+Na). HRMS C30H40N2O4 m/z 515.2886 (M+Na)Cal; 515.2891 (M+Na)Obs.

Sources & evidence

ORD record: ord-87550c72fd354a1d852207929122d2f1
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07282512B2

Reaction notes

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