(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide → HCID 21021937, compound

HRID 1061311Notes

Reaction equation

HRID 1061311 reaction equation
[CH2:1]([O:3][C:4](=[O:20])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[CH3:2].[NH2:21][CH2:22][C@@H:23]([C:25]1[CH:26]=[CH:27][C:28]([OH:36])=[C:29]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[CH:30]=1)[OH:24]>>[CH2:1]([O:3][C:4](=[O:20])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][CH:16]([NH:21][CH2:22][C@H:23]([OH:24])[C:25]3[CH:26]=[CH:27][C:28]([OH:36])=[C:29]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[CH:30]=3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamideHCID 69654874HCID 69654874, compound

Product 1

HCID 21021937HCID 21021937, compound

Procedure

The title compound was prepared from (E)-3-[4-(4-oxo-piperidine-1-yl)-phenyl]-acrylic acid ethyl ester (which was obtained in Example 169) (0.27 g, 1.0 mmol) and N-[5-((1R)-2-Amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Example 10) (0.27 g, 1.1 mmol) according to the prodedure shown for Example 180 to give 0.40 g of yellow solid; m.p. 103-106° C.; 1H NMR (DMSO-d6) δ 1.24 (t, 3H), 1.20-1.45 (m, 2H), 1.75-1.95 (m, 2H), 2.55-2.95 (m, 5H), 2.92 (t, 3H), 3.67-3.85 (m, 2H), 4.14 (q, 2H), 4.46-4.50 (m, 1H), 6.34 (d, 1H), 6.96 (d, 1H), 6.79-7.05 (m, 3H), 7.05 (d, 1H), 7.17 (d, 1H), 7.56 (d, 2H); MS (ES) m/z: 504.0 (MH+).

Sources & evidence

ORD record
ord-8a73d5bf6d8d41cba9b28402beee62be
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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