Formic Acid → HCID 25069853, compound

HRID 2047324Notes

Reaction equation

HRID 2047324 reaction equation
C[O:2][C:3]([CH:5]1[CH2:8][N:7]([CH2:9][C@H:10]([OH:39])[CH2:11][O:12][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([C:20]3[N:24]=[C:23]([C:25]4[CH:30]=[C:29]([CH3:31])[N:28]=[C:27]([N:32]([CH2:35][CH3:36])[CH2:33][CH3:34])[CH:26]=4)[O:22][N:21]=3)=[CH:15][C:14]=2[CH2:37][CH3:38])[CH2:6]1)=[O:4].C(O)=O>CO.C1COCC1.[Li+].[OH-]>[CH2:35]([N:32]([CH2:33][CH3:34])[C:27]1[CH:26]=[C:25]([C:23]2[O:22][N:21]=[C:20]([C:16]3[CH:17]=[C:18]([CH3:19])[C:13]([O:12][CH2:11][C@@H:10]([OH:39])[CH2:9][N:7]4[CH2:6][CH:5]([C:3]([OH:4])=[O:2])[CH2:8]4)=[C:14]([CH2:37][CH3:38])[CH:15]=3)[N:24]=2)[CH:30]=[C:29]([CH3:31])[N:28]=1)[CH3:36]

Participants

6

Reactant 2

HCID 284Formic AcidHCID 68578663HCID 68578663, compound

Product 1

HCID 25069853HCID 25069853, compoundYield 11.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-((S)-3-{4-[5-(2-diethylamino-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-2-hydroxy-propyl)-azetidine-3-carboxylic acid methyl ester (60 mg, 0.113 mmol) in methanol (2 mL), THF (2 mL) and 2 M aq. LiOH solution (1 mL) is stirred at rt for 2 h before the reaction mixture is neutralized by adding formic acid. The mixture is concentrated and the crude product is purified by prep. HPLC followed by precipitation of the product from EA/heptane to give the title compound (7 mg) as a pale yellow solid; LC-MS: tR=0.72 min; [M+1]+=524.24.

Workup

  1. concentrationThe mixture is concentrated
  2. customthe crude product is purified by prep
  3. customHPLC followed by precipitation of the product from EA/heptane

Sources & evidence

ORD record
ord-81527c5e68b0489ba2b340672263480f
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

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