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

Hydrochloric Acid → (R)-2-[(7-Hydroxy-3-phenyl-isoxazolo[4,5-c]pyridine-6-carbonyl)-amino]-propionic acid

HRID 2388171
Notes
Print preview

Reaction equation

HRID 2388171 reaction equation
[OH:1][C:2]1[C:3]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:4]=2[CH:5]=[N:6][C:7]=1[C:8]([O:10]CC)=O.[NH2:22][C@H:23]([C:25]([OH:27])=[O:26])[CH3:24].[O-]CC.[Na+].Cl>CN(C=O)C.O>[OH:1][C:2]1[C:3]2[O:15][N:14]=[C:13]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:4]=2[CH:5]=[N:6][C:7]=1[C:8]([NH:22][C@H:23]([CH3:24])[C:25]([OH:27])=[O:26])=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5950L-AlanineHCID 2723922Sodium ethoxideHCID 67530168HCID 67530168, compound

Product 1

HCID 42635756(R)-2-[(7-Hydroxy-3-phenyl-isoxazolo[4,5-c]pyridine-6-carbonyl)-amino]-propionic acidYield 48%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

Ethyl 7-hydroxy-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (0.1 g, 0.35 mmol) was dissolved in 10 mL of DMF. L-Alanine (0.627 g, 7.04 mmol) and sodium ethoxide (0.36 g, 5.28 mmol) were added and the mixture was refluxed for 3 h. The mixture was cooled to room temperature and diluted with 70 mL of water. Concentrated hydrochloric acid was added dropwise until pH was 2. The resulting suspension was filtered and the solid was dried under vacuum to give 55 mg of the title compound. MS: (+) m/z 328.00 (M+1).

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. filtrationThe resulting suspension was filtered
  3. customthe solid was dried under vacuum

Sources & evidence

ORD record
ord-a1102e179ce0439e89fc1f4a0a5fe970
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08269008B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes