(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide → HCID 69654864, compound

HRID 1061402Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[S:10](=[O:26])(=[O:25])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]2)=[CH:14][CH:13]=1)=[O:4].[NH2:27][CH2:28][C@@H:29]([C:31]1[CH:32]=[CH:33][C:34]([OH:42])=[C:35]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH:36]=1)[OH:30]>>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[S:10]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([N:18]2[CH2:19][CH2:20][CH:21]([NH:27][CH2:28][C@H:29]([OH:30])[C:31]3[CH:32]=[CH:33][C:34]([OH:42])=[C:35]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH:36]=3)[CH2:22][CH2:23]2)=[CH:16][CH:17]=1)(=[O:25])=[O:26])=[O:4]

Participants

Reactant 2

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

HCID 69655037HCID 69655037, compound

Product 1

HCID 69654864HCID 69654864, compound

Procedure

The title compound was prepared from 3-[4-(4-oxo-piperidine-1-yl)-phenylsulfamoyl]-thiophene-2-carboxylic acid methyl ester (which was obtained in Example 234) 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 278 as a pale yellowish solid; 1H NMR (300 MHz, DMSO-d6) δ 1.20-1.40 (m, 2H), 1.70-1.90 (m, 2H), 2.50-2.75 (m, 5H), 3.40-3.55 (m, 2H), 3.89 (s, 2H), 4.46 (dd, J=8.0, 4.2 Hz, 1H), 6.75-6.85 (m, 3H), 6.90 (d, J=9.0 Hz, 2H), 7.00 (dd, J=8.3, 2.0 Hz, 1H), 7.16 (d, J=2.0 Hz, 1H), 7.32 (d, J=3.3 Hz, 1H), 7.89 (d, J=3.3 Hz, 1H); MS (ES) m/z: 624.9 (MH+); HRMS Calcd. for C26H34N4O8S3 (MH+): 625.1455. Found: 625.1441.

Sources & evidence

ORD record: ord-5b2bf803f8ff4a428d263ccbcd49b28a
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525202B2

Reaction notes

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