Hydrochloric Acid → 3-(2-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}-1-methylpropoxy)propionic acid

HRID 1926980Notes

Reaction equation

HRID 1926980 reaction equation
Cl.C([O:6][C:7](=[O:39])[CH2:8][CH2:9][O:10][CH:11]([CH3:38])[CH:12]([O:14][C:15]1[C:16]2[C:23]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)=[C:22]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[O:21][C:17]=2[N:18]=[CH:19][N:20]=1)[CH3:13])(C)(C)C>O1CCOCC1>[CH3:31][O:30][C:27]1[CH:26]=[CH:25][C:24]([C:23]2[C:16]3[C:15]([O:14][CH:12]([CH3:13])[CH:11]([CH3:38])[O:10][CH2:9][CH2:8][C:7]([OH:39])=[O:6])=[N:20][CH:19]=[N:18][C:17]=3[O:21][C:22]=2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 250964163-(2-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}-1-methylpropoxy)propionic acid tert.-butyl ester

Product 1

HCID 580167713-(2-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}-1-methylpropoxy)propionic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Add 4.0 ml 4 N hydrogen chloride in dioxan to 500 mg (0.96 mmol) 3-(2-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}-1-methylpropoxy)propionic acid tert.-butyl ester 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). 249 mg (56% of theor.) of the desired product is obtained as (R,S/S,R) racemate.

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-3ccfa9aa74d640fdb9979c57d10a8143
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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