Methanol → HCID 178447703, compound

HRID 1744080Notes

Reaction equation

HRID 1744080 reaction equation
[CH3:1][CH:2]([CH3:21])[CH2:3][CH:4]([S:9][C:10]1[NH:14][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:12][N:11]=1)[C:5]([O:7]C)=[O:6].CO.O1CCCC1.[Li]>O.Cl>[CH3:1][CH:2]([CH3:21])[CH2:3][CH:4]([S:9][C:10]1[NH:14][C:13]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[N:12][N:11]=1)[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 3028194LithiumHCID 178500365HCID 178500365, compound

Product 1

HCID 178447703HCID 178447703, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

Methyl 4-methyl-2-[(5-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl]pentanoate (473 mg, 1.54 mmoles) in a mixture of water (2 mL), methanol (2 mL) and tetrahydrofuran (4 mL) was treated with lithium hydroxyde monohydrate (193 mg, 4.6 mmoles) until disappearance of the starting material was observed by TLC. The reaction was diluted with 1.2 N hydrochloric acid until pH 1. The aqueous phase was extracted 3 times with dichloromethane. The organic phase was concentrated under reduced pressure to yield a crude residue of 4-methyl-2-[(5-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl]pentanoic acid which was used as such in the next reaction.

Workup

  1. extractionThe aqueous phase was extracted 3 times with dichloromethane
  2. concentrationThe organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-260f832cff254b32b7e417d72b6cecc0
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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