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

HRID 1926977Notes

Reaction equation

HRID 1926977 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]([CH2:29][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>[CH2:29]([C:26]1[CH:27]=[CH:28][C:23]([C:22]2[C:15]3[C:14]([O:13][C@H:11]([CH3:12])[CH2:10][CH2:9][CH2:8][CH2:7][C:6]([OH:38])=[O:5])=[N:19][CH:18]=[N:17][C:16]=3[O:20][C:21]=2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])=[CH:24][CH:25]=1)[CH3:30]

Participants

4

Reactant 1

HCID 58016900(6R)-6-{[5-(4-Ethylphenyl)-6-(2-fluorophenyl)furo[2,3-d]pyrimidin-4-yl]oxy}heptanoic acid tert.-butyl ester

Product 1

HCID 16656765(-)-(6R)-6-{[5-(4-Ethylphenyl)-6-(2-fluorophenyl)furo[2,3-d]pyrimidin-4-yl]oxy}heptanoic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Dissolve 420 mg (0.81 mmol) (6R)-6-{[5-(4-ethylphenyl)-6-(2-fluorophenyl)furo[2,3-d]pyrimidin-4-yl]oxy}heptanoic acid tert.-butyl ester in 5.3 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). 200 mg (53% 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-e90e17963ef3461db10e3d309ba88b79
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

Loading…