(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide → HCID 10231287, compound

HRID 1061259Notes

Reaction equation

HRID 1061259 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:26][CH2:25][C:20]4(OCCO4)[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)=[N:9][N:8]=[N:7]1)[CH3:2].[NH2:28][CH2:29][C@@H:30]([C:32]1[CH:33]=[CH:34][C:35]([OH:43])=[C:36]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])[CH:37]=1)[OH:31]>>[OH:31][C@H:30]([C:32]1[CH:33]=[CH:34][C:35]([OH:43])=[C:36]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])[CH:37]=1)[CH2:29][NH:28][CH:20]1[CH2:19][CH2:18][N:17]([C:14]2[CH:15]=[CH:16][C:11]([C:10]3[N:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:27])[N:7]=[N:8][N:9]=3)=[CH:12][CH:13]=2)[CH2:26][CH2:25]1

Participants

3

Reactant 2

HCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamideHCID 131723779HCID 131723779, compound

Product 1

HCID 10231287HCID 10231287, compound

Procedure

The title compound was prepared from ethyl{5-[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)phenyl]-1H-tetraazol-1-yl}acetate (which was obtained in Example 48) and N-[5-((1R)-2-amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Example 10) according to the procedures of Example 34 and Example 73 as a white solid; mp >140° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.17 (t, J=7.1 Hz, 3H), 1.20-1.40 (m, 2H), 1.80-1.95 (m, 2H), 2.50-3.50 (m, 5H), 2.89 (s, 3H), 3.70-3.90 (m, 2H), 4.11 (q, J=7.1 Hz, 2H), 4.47 (dd, J=7.8, 4.4 Hz, 1H), 5.60 (brs, 2H), 6.79 (d, J=8.2 Hz, 1H), 6.96 (dd, J=8.2, 2.0 Hz, 1H), 7.07 (d, J=8.9 Hz, 2H), 7.16 (d, J=2.0 Hz, 1H), 7.56 (d, J=8.9 Hz, 2 H); MS (ES) m/z: 560.2 (MH+); HRMS Calcd. for C21H28N7O4S(MH+): 560.2286. Found: 560.2282.

Sources & evidence

ORD record
ord-797d4f811921457bb4798b26c193e21c
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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