(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide → HCID 69655138, compound

HRID 1061320Notes

Reaction equation

HRID 1061320 reaction equation
C([O:8][C:9](=[O:28])[CH2:10][CH2:11][NH:12][C:13](=[O:27])[C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]2)=[CH:16][CH:15]=1)C1C=CC=CC=1.[NH2:29][CH2:30][C@@H:31]([C:33]1[CH:34]=[CH:35][C:36]([OH:44])=[C:37]([NH:39][S:40]([CH3:43])(=[O:42])=[O:41])[CH:38]=1)[OH:32]>>[OH:32][C@H:31]([C:33]1[CH:34]=[CH:35][C:36]([OH:44])=[C:37]([NH:39][S:40]([CH3:43])(=[O:42])=[O:41])[CH:38]=1)[CH2:30][NH:29][CH:23]1[CH2:22][CH2:21][N:20]([C:17]2[CH:16]=[CH:15][C:14]([C:13]([NH:12][CH2:11][CH2:10][C:9]([OH:8])=[O:28])=[O:27])=[CH:19][CH:18]=2)[CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamideHCID 69654859HCID 69654859, compound

Product 1

HCID 69655138HCID 69655138, compound

Procedure

The title compound was prepared from 3-[4-(4-oxo-piperidine-1-yl)-benzoylamino]-propionic acid benzyl ester (which was obtained in Example 159) 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 >170° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.20-1.45 (m, 2H), 1.80-1.95 (m, 2H), 2.43 (t, J=7.0 Hz, 2H), 2.60-2.90 (m, 5H), 2.90 (s, 3H), 3.00-3.40 (m, 2H), 3.70-3.85 (m, 2H), 4.50 (dd, J=8.0, 4.2 Hz, 1H), 6.82 (d, J=8.3 Hz, 1H), 6.92 (d, J=8.9 Hz, 2H), 7.01 (dd, J=8.3, 1.9 Hz, 1H), 7.18 (d, J=1.9 Hz, 1H), 7.68 (d, J=8.9 Hz, 2H), 8.26 (t, J=5.2 Hz, 1H); MS (ES) m/z: 521.2 (MH+); HRMS Calcd. for C24H33N4O7S(MH+): 521.2064. Found: 521.2056.

Sources & evidence

ORD record
ord-70761872900948a6a096d6527490e087
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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