HCID 58979703, compound → [1-(2,6-Difluorobenzyl)cyclobutyl]methyl(1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)-5-{[(methylamino)carbonyl]amino}pentylcarbamate

HRID 1180753Notes

Reaction equation

HRID 1180753 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[C:3]=1[CH2:4][C:5]1([CH2:9][OH:10])[CH2:8][CH2:7][CH2:6]1.C(C1([CH2:29][OH:30])CCCCC1)C1C=CC=CC=1.Cl.[NH2:32][C@@H:33]([CH2:47][CH2:48][CH2:49][CH2:50][NH:51][C:52]([NH:54][CH3:55])=[O:53])[CH:34]([OH:46])[C:35]([NH:37][C@@H:38]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH3:39])=[O:36].Cl.N[C@H](C(O)C(=O)N[C@@H](C1C=CC=CC=1)C)CCCCNC(N1CCOCC1)=O>>[OH:46][CH:34]([C@@H:33]([NH:32][C:29](=[O:30])[O:10][CH2:9][C:5]1([CH2:4][C:3]2[C:2]([F:1])=[CH:14][CH:13]=[CH:12][C:11]=2[F:15])[CH2:6][CH2:7][CH2:8]1)[CH2:47][CH2:48][CH2:49][CH2:50][NH:51][C:52]([NH:54][CH3:55])=[O:53])[C:35](=[O:36])[NH:37][C@@H:38]([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[CH3:39]

Participants

5

Reactant 4

HCID 58979703HCID 58979703, compoundHCID 58979707(1-Benzylcyclohexyl)methanolHCID 69202106HCID 69202106, compoundHCID 69236903N-((5S)-5-amino-6-hydroxy-7-oxo-7-{[(1R)-1-phenylethyl]amino}heptyl)-4-morpholinecarboxamide hydrochloride

Product 1

HCID 58979660[1-(2,6-Difluorobenzyl)cyclobutyl]methyl(1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)-5-{[(methylamino)carbonyl]amino}pentylcarbamate

Procedure

[1-(2,6-Difluorobenzyl)cyclobutyl]methyl(1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)-5-{[(methylamino)carbonyl]amino}pentylcarbamate was prepared as in example 9i except that [1-(2,6-difluorobenzyl)cyclobutyl]methanol was substituted for (1-benzylcyclohexyl)methanol, and (3S)-3-amino-2-hydroxy-7-{[(methylamino)carbonyl]amino}-N-[(1R)-1-phenylethyl]heptanamide hydrochloride was substituted for N-((5S)-5-amino-6-hydroxy-7-oxo-7-{[(1R)-1-phenylethyl]amino}heptyl)-4-morpholinecarboxamide hydrochloride. 1H NMR (300 MHz, DMSO-d6) δ 8.06 (m, 1H), 7.01-7.45 (m, 8H), 6.43 (d, J=8 Hz, 1H), 5.83 (m, 1H), 5.60 (m, 2H), 4.94 (m, 1H), 3.70-4.00 (m, 4H), 3.35 under water peak (m, 3H), 2.65-3.00 (m, 4H), 1.60-1.85 (m, 6H), 1.10-1.50 (m, 9H). ES-LCMS m/z 573 (M−H).

Sources & evidence

ORD record
ord-1cb28f65428a4a71ae33e4b3eea0301a
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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