Hydrochloric Acid → (R)-3-[2-Cyclopropyl-7-(1,4-dimethyl-1H-indol-3-ylmethyl)-8-oxo-7,8-dihydro-purin-9-yl]-3-phenyl-propionic acid

HRID 2175205Notes

Reaction equation

HRID 2175205 reaction equation
C([O:3][C:4](=[O:38])[CH2:5][C@@H:6]([N:13]1[C:21](=[O:22])[N:20]([CH2:23][C:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][C:31]=3[CH3:33])[N:26]([CH3:34])[CH:25]=2)[C:19]2[C:14]1=[N:15][C:16]([CH:35]1[CH2:37][CH2:36]1)=[N:17][CH:18]=2)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[Li+].[OH-].Cl>C1COCC1.O>[CH:35]1([C:16]2[N:15]=[C:14]3[C:19]([N:20]([CH2:23][C:24]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][C:31]=5[CH3:33])[N:26]([CH3:34])[CH:25]=4)[C:21](=[O:22])[N:13]3[C@@H:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:5][C:4]([OH:38])=[O:3])=[CH:18][N:17]=2)[CH2:36][CH2:37]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58497405(R)-3-[2-Cyclopropyl-7-(1,4-dimethyl-1H-indol-3-ylmethyl)-8-oxo-7,8-dihydro-purin-9-yl]-3-phenyl-propionic acid ethyl ester

Product 1

HCID 58497445(R)-3-[2-Cyclopropyl-7-(1,4-dimethyl-1H-indol-3-ylmethyl)-8-oxo-7,8-dihydro-purin-9-yl]-3-phenyl-propionic acidYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(R)-3-[2-Cyclopropyl-7-(1,4-dimethyl-1H-indol-3-ylmethyl)-8-oxo-7,8-dihydro-purin-9-yl]-3-phenyl-propionic acid ethyl ester (130 mg, 0.255 mmol) was dissolved in THF (3 ml). To the solution a concentrated solution of LiOH in water (2 ml) was added. The mixture was stirred at room temperature for 1 hour. The reaction was monitored by TLC. The reaction mixture was neutralized with 1N HCl, and then extracted with ethyl acetate 3×. The organic layer was dried over MgSO4, filtered and evaporated to dryness. The white solid obtained was purified by prep TLC, eluded with 10% methanol in dichloromethane to give the title compound (52 mg, 43%). LCMS, M++1, m/z: 481.54

Workup

  1. extractionextracted with ethyl acetate 3×
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe white solid obtained
  6. customwas purified by prep TLC

Sources & evidence

ORD record
ord-45e623da7a7a49b199e699306022ec54
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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