HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Water → N-(5-((1R,2S)-2-(3,5-Dimethoxybenzylamino)-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamide

HRID 1685895
Notes
Print preview

Reaction equation

HRID 1685895 reaction equation
[NH2:1][C@@H:2]([CH3:17])[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].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([O:28][CH3:29])[CH:27]=1)[CH:23]=O.O>CO>[CH3:29][O:28][C:26]1[CH:25]=[C:22]([CH:21]=[C:20]([O:19][CH3:18])[CH:27]=1)[CH2:23][NH:1][C@@H:2]([CH3:17])[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 817473,5-DimethoxybenzaldehydeHCID 58280635N-(5-((1R,2S)-2-Amino-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamide

Product 1

HCID 58280637N-(5-((1R,2S)-2-(3,5-Dimethoxybenzylamino)-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamideYield 57.7%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

To a solution of the amine (4) (363 mg, 1.39 mmol) and 3,5-dimethoxybenzaldehyde (301 mg, 1.81 mmol) in methanol (10 mL) was added borane-pyridine complex (445 μL, 4.18 mmol) at 40° C. and the resulting mixture was stirred for 2 hours. The reaction mixture was cooled to room temperature and water was added thereto, followed by extraction with a mixed solvent (ethyl acetate:methanol=10:1) and subsequent washing of the organic layer with saturated brine. The organic layer was dried and concentrated and the obtained crude product was purified by amine silica gel column chromatography (eluent; chloroform:methanol=7:1) to obtain the desired amine (5) as a pale yellow solid (329 mg, Yield: 57%).

Workup

  1. extractionfollowed by extraction with a mixed solvent (ethyl acetate:methanol=10:1)
  2. washsubsequent washing of the organic layer with saturated brine
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customthe obtained crude product
  6. customwas purified by amine silica gel column chromatography (eluent; chloroform:methanol=7:1)

Sources & evidence

ORD record
ord-8cb10361401249c297301eb1044f4f19
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08148427B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes