Hydrochloric Acid → [2-({[5-(4-Ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)-3,3-dimethylbutoxy]-acetic acid

HRID 1926979Notes

Reaction equation

HRID 1926979 reaction equation
Cl.C([O:6][C:7](=[O:41])[CH2:8][O:9][CH2:10][CH:11]([CH2:16][O:17][C:18]1[C:19]2[C:26]([C:27]3[CH:32]=[CH:31][C:30]([CH2:33][CH3:34])=[CH:29][CH:28]=3)=[C:25]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[O:24][C:20]=2[N:21]=[CH:22][N:23]=1)[C:12]([CH3:15])([CH3:14])[CH3:13])(C)(C)C>O1CCOCC1>[CH2:33]([C:30]1[CH:29]=[CH:28][C:27]([C:26]2[C:19]3[C:18]([O:17][CH2:16][CH:11]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:10][O:9][CH2:8][C:7]([OH:41])=[O:6])=[N:23][CH:22]=[N:21][C:20]=3[O:24][C:25]=2[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[CH:32][CH:31]=1)[CH3:34]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58016779[2-({[5-(4-Ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)-3,3-dimethylbutoxy]-acetic acid tert.-butyl ester

Product 1

HCID 58016811[2-({[5-(4-Ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)-3,3-dimethylbutoxy]-acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Add 1.0 ml 4 N hydrogen chloride in dioxan to 155 mg (0.29 mmol) [2-({[5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}methyl)-3,3-dimethylbutoxy]acetic acid tert.-butyl ester and stir for 48 h at RT. After concentrating the reaction solution by evaporation under vacuum, purify the residue by preparative RP-HPLC (gradient: water/acetonitrile). 122 mg (88% of theor.) of the desired product (racemate) 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-e75aeb001cf2473cbcf75d7bc628d8cd
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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