HCID 10626009, compound → HCID 10627031, compound

HRID 1061319Notes

Reaction equation

HRID 1061319 reaction equation
C([O:8][C:9](=[O:39])[C@@H:10]([NH:23][C:24](=[O:38])[C:25]1[CH:30]=[CH:29][C:28]([N:31]2[CH2:36][CH2:35][C:34](=O)[CH2:33][CH2:32]2)=[CH:27][CH:26]=1)[CH2:11][CH2:12][C:13]([O:15]CC1C=CC=CC=1)=[O:14])C1C=CC=CC=1.[NH2:40][CH2:41][C@@H:42]([C:44]1[CH:45]=[CH:46][C:47]([OH:55])=[C:48]([NH:50][S:51]([CH3:54])(=[O:53])=[O:52])[CH:49]=1)[OH:43]>>[OH:43][C@H:42]([C:44]1[CH:45]=[CH:46][C:47]([OH:55])=[C:48]([NH:50][S:51]([CH3:54])(=[O:53])=[O:52])[CH:49]=1)[CH2:41][NH:40][CH:34]1[CH2:33][CH2:32][N:31]([C:28]2[CH:29]=[CH:30][C:25]([C:24]([NH:23][C@@H:10]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[C:9]([OH:39])=[O:8])=[O:38])=[CH:26][CH:27]=2)[CH2:36][CH2:35]1

Participants

3

Reactant 2

HCID 10626009HCID 10626009, compoundHCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide

Product 1

HCID 10627031HCID 10627031, compound

Procedure

The title compound was prepared from (2S)-2-[4-(4-oxo-piperidine-1-yl)-benzoylamino]-pentanedioic acid dibenzyl ester (which was obtained in Example 156) and N-[ 5-((1R)-2-amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Example 10) according to the procedure of Example 179 as a white solid; mp >230° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.40-1.60 (m, 2H), 1.90-2.10 (m, 4H), 2.31 (t, J=7.5 Hz, 2H), 2.65-3.20 (m, 7H), 3.00 (s, 3H), 3.85-4.00 (m, 2H), 4.25-4.35 (m, 1H), 4.65-4.80 (m, 1H), 6.88 (d, J=8.4 Hz, 1H), 6.95 (d, J=8.7 Hz, 2H), 7.08 (dd, J=8.4, 1.2 Hz, 1H), 7.25 (d, J=1.8 Hz, 1H), 7.74 (d, J=8.7 Hz, 2H), 8.14 (d, J=7.2 Hz, 1H); MS (ES) m/z: 579.1 (MH+); HRMS Calcd. for C26H35N4O9S(MH+): 579.1973. Found: 579.1955.

Sources & evidence

ORD record
ord-0080e2a5dfaf483d93e7ba91f99ee65a
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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