(6R)-6-{[6-(2-Fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]oxy}heptanoic acid tert.-butyl ester → (6R)-6-{[6-(2-Fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]oxy}heptanoic acid

HRID 1926974Notes

Reaction equation

HRID 1926974 reaction equation
C([O:5][C:6](=[O:38])[CH2:7][CH2:8][CH2:9][CH2:10][C@H:11]([O:13][C:14]1[C:15]2[C:22]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)=[C:21]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[F:37])[O:20][C:16]=2[N:17]=[CH:18][N:19]=1)[CH3:12])(C)(C)C>Cl.O1CCOCC1>[F:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[C:21]1[O:20][C:16]2[N:17]=[CH:18][N:19]=[C:14]([O:13][C@H:11]([CH3:12])[CH2:10][CH2:9][CH2:8][CH2:7][C:6]([OH:38])=[O:5])[C:15]=2[C:22]=1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1

Participants

4

Reactant 1

HCID 25096414(6R)-6-{[6-(2-Fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]oxy}heptanoic acid tert.-butyl ester

Product 1

HCID 58016806(6R)-6-{[6-(2-Fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]oxy}heptanoic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Dissolve 373 mg (0.72 mmol) (6R)-6-{[6-(2-fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]oxy}heptanoic acid tert.-butyl ester in 4 ml 4 N hydrogen chloride in dioxan and stir for 16 h at RT. After concentrating the reaction solution by evaporation under vacuum, purify the residue by preparative RP-HPLC (gradient: water/acetonitrile). 171 mg (51% of theor.) of the desired product is obtained.

Workup

  1. concentrationAfter concentrating the reaction solution
  2. customby evaporation under vacuum
  3. custompurify the residue by preparative RP-HPLC (gradient: water/acetonitrile)

Sources & evidence

ORD record
ord-0930dffe2fd04dd9b5860e4975ce3514
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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