Methanol → HCID 67494873, compound

HRID 1776029Notes

Reaction equation

HRID 1776029 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][N:15]=2)[C@H:10]([CH3:23])[CH2:9]1)=O)(C)(C)C.S(=O)(=O)(O)O.[OH-].[Na+].[CH3:31]O>>[CH3:31][O:22][C:20](=[O:21])[C:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][C@H:10]2[CH3:23])=[N:15][CH:16]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 67495464HCID 67495464, compound

Product 1

HCID 67494873HCID 67494873, compound

Conditions

Temperature
64 °C

Procedure

To a mixture of (R)-4-(5-carboxy-pyridin-2-yl)-3-methyl-piperazine-1-carboxylic acid tert-butyl ester (50 g, 0.156 mol) and methanol (500 mL) was slowly added concentrated sulfuric acid (37 mL). The reaction mixture was warmed to 64° C., stirred at 64° C. overnight, cooled to RT and then ice water (800 mL) was added followed by 50% aqueous sodium hydroxide (60 mL). The reaction mixture was extracted with ethyl acetate (3×800 mL). Combined organic layers were dried over sodium sulfate and evaporated to give the title intermediate as an oil. HPLC Method A: Retention time 3.50 and 3.72 min.

Workup

  1. temperaturecooled to RT
  2. extractionThe reaction mixture was extracted with ethyl acetate (3×800 mL)
  3. dry with materialCombined organic layers were dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-736815b27b824c64929bc778baae312e
Source dataset
uspto-grants-2016_02
Patent number
US09260414B2

Reaction notes

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