4-{[(2S)-2-{[6-(2-Fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]oxy}propyl]-(methyl)amino}butyric acid tert.-butyl ester → (+)-4-{[(2S)-2-{[6-(2-Fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]oxy}propyl]-(methyl)amino}butyric acid

HRID 1926975Notes

Reaction equation

HRID 1926975 reaction equation
C([O:5][C:6](=[O:40])[CH2:7][CH2:8][CH2:9][N:10]([CH2:12][C@@H:13]([O:15][C:16]1[C:17]2[C:24]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[C:23]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[F:39])[O:22][C:18]=2[N:19]=[CH:20][N:21]=1)[CH3:14])[CH3:11])(C)(C)C>Cl.O1CCOCC1>[F:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[C:23]1[O:22][C:18]2[N:19]=[CH:20][N:21]=[C:16]([O:15][C@@H:13]([CH3:14])[CH2:12][N:10]([CH3:11])[CH2:9][CH2:8][CH2:7][C:6]([OH:40])=[O:5])[C:17]=2[C:24]=1[C:25]1[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=1

Participants

4

Reactant 1

HCID 580168184-{[(2S)-2-{[6-(2-Fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]oxy}propyl]-(methyl)amino}butyric acid tert.-butyl ester

Product 1

HCID 58016840(+)-4-{[(2S)-2-{[6-(2-Fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]oxy}propyl]-(methyl)amino}butyric acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Dissolve 102 mg (93% purity, 0.19 mmol) 4-{[(2S)-2-{[6-(2-fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]oxy}propyl](methyl)amino}butyric acid tert.-butyl ester in 2 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). 48 mg (52% 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-8021c50ff605496da3d98a5c09492a1c
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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