Acetic Acid → HCID 10227562, compound

HRID 1634838Notes

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].COC([C:21]1[C:22]([N:27]2[CH2:32][CH2:31][CH:30]([CH:33]=O)[CH2:29][CH2:28]2)=[N:23][CH:24]=[CH:25][CH:26]=1)=O.[C:35]([OH:38])(=[O:37])C.[C:39]([BH3-])#N.[Na+]>>[OH:4][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)[CH2:2][NH:1][CH2:33][CH:30]1[CH2:29][CH2:28][N:27]([C:22]2[CH:21]=[CH:26][C:25]([C:35]([O:38][CH3:39])=[O:37])=[CH:24][N:23]=2)[CH2:32][CH2:31]1

Participants

Reactant 4

HCID 176Acetic Acid

HCID 5003444Sodium cyanoborohydride

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

HCID 18678536HCID 18678536, compound

Product 1

HCID 10227562HCID 10227562, compoundYield 33.5%

Procedure

Prepared from N-[5-(2-amino-1-{R}-hydroxyethyl)-2-hydroxyphenyl]-methanesulfonamide (0.119 g, 0.48 mmol), 1-(3-methoxycarbonyl-2-pyridyl)-4-formylpiperidine (0.12 g, 0.48 mmol), glacial acetic acid (0.03 g, 0.48 mmol) and sodium cyanoborohydride (0.03 g, 0.48 mmol) according to the procedure used for example 67 (Step B) to give 0.077 g of the title compound as a yellow solid (isolated as the HCl salt).

Sources & evidence

ORD record: ord-8b47980e133746ccb3a5db90cc84ea19
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06506901B2

Reaction notes

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