Acetic Acid → HCID 59032966, compound

HRID 1634834Notes

Reaction equation

HRID 1634834 reaction equation
[NH2:1][CH2:2][C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[OH:4].[CH3:17][O:18][C:19](=[O:44])[CH2:20][CH2:21][C:22]1[O:26][N:25]=[C:24]([C:27]2[CH:32]=[CH:31][C:30]([S:33]([N:36]3[CH2:41][CH2:40][CH:39]([CH:42]=O)[CH2:38][CH2:37]3)(=[O:35])=[O:34])=[CH:29][CH:28]=2)[N:23]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>>[CH3:17][O:18][C:19](=[O:44])[CH2:20][CH2:21][C:22]1[O:26][N:25]=[C:24]([C:27]2[CH:28]=[CH:29][C:30]([S:33]([N:36]3[CH2:37][CH2:38][CH:39]([CH2:42][NH:1][CH2:2][C@H:3]([OH:4])[C:5]4[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=4)[CH2:40][CH2:41]3)(=[O:34])=[O:35])=[CH:31][CH:32]=2)[N:23]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamideHCID 86584785HCID 86584785, compound

Product 1

HCID 59032966HCID 59032966, compoundYield 51.3%

Procedure

Prepared from N-[5-(2-amino-1-{R}-hydroxyethyl)-2-hydroxyphenyl]-methane-sulfonamide (0.136 g, 0.55 mmol), 3-[3-(4-{[4-formyl-1-piperidinyl]-sulfonyl}phenyl)-1,2,4-oxadiazol-5-yl]propanoic acid methyl ester (0.55 mmol), glacial acetic acid (0.040 g, 0.66 mmol) and sodium cyanoborohydride (0.0382 g, 0.061 mmol) according to the procedure used for example 67 (Step B) to give 0.180 g of the title compound as a white solid.

Sources & evidence

ORD record
ord-cb781136f8db4f43b7eea9215f43e590
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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