HCID 10712597, compound → HCID 10816992, compound

HRID 1061325Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:25])[C@@H:5]([NH:9][C:10](=[O:24])[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]2)=[CH:13][CH:12]=1)[CH:6]([CH3:8])[CH3:7])[CH3:2].[NH2:26][CH2:27][C@@H:28]([C:30]1[CH:31]=[CH:32][C:33]([OH:41])=[C:34]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])[CH:35]=1)[OH:29]>>[CH2:1]([O:3][C:4](=[O:25])[C@@H:5]([NH:9][C:10](=[O:24])[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][CH:20]([NH:26][CH2:27][C@H:28]([OH:29])[C:30]3[CH:31]=[CH:32][C:33]([OH:41])=[C:34]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])[CH:35]=3)[CH2:19][CH2:18]2)=[CH:13][CH:12]=1)[CH:6]([CH3:8])[CH3:7])[CH3:2]

Participants

Reactant 2

HCID 10712597HCID 10712597, compound

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

Product 1

HCID 10816992HCID 10816992, compound

Procedure

The title compound was prepared from 3-methyl-(2S)-2-[4-(4-oxo-piperidine-1-yl)-benzoylamino]-butyric acid ethyl ester (which was obtained in Example 163) 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 180 as an off-white solid; mp >85° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 0.92 (d, J=6.8 Hz, 3H), 0.97 (d, J=6.8 Hz, 3H), 1.17 (t, J=7.1 Hz, 3H), 1.20-1.40 (m, 2H), 1.75-1.95 (m, 2H), 2.05-2.20 (m, 1H), 2.55-2.90 (m, 5H), 2.90 (s, 3H), 3.70-3.85 (m, 2H), 4.00-4.20 (m, 2H), 4.22 (t, J=7.7 Hz, 1H), 4.48 (dd, J=8.0, 4.4 Hz, 1H), 6.80 (d, J=8.2 Hz, 1H), 6.95 (d, J=8.9 Hz, 2H), 6.98 (dd, J=8.2, 2.0 Hz, 1H), 7.17 (d, J=2.0 Hz, 1H), 7.76 (d, J=8.9 Hz, 2H), 8.17 (d, J=7.9 Hz, 1H); MS (ES) m/z: 577.2 (MH+); HRMS Calcd. for C29H43N4O7S(MH+): 577.2690. Found: 577.2682.

Sources & evidence

ORD record: ord-d6006d0ebfc04997809ec00855e2c669
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525202B2

Reaction notes

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