Hydrochloric Acid → HCID 58016765, compound

HRID 1926967Notes

Reaction equation

HRID 1926967 reaction equation
C([O:5][C:6](=[O:37])[CH2:7][O:8][CH2:9][CH:10]([CH3:36])[CH2:11][O:12][C:13]1[C:14]2[C:21]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)=[C:20]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[O:19][C:15]=2[N:16]=[CH:17][N:18]=1)(C)(C)C.Cl>O1CCOCC1>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([C:21]2[C:14]3[C:13]([O:12][CH2:11][CH:10]([CH3:36])[CH2:9][O:8][CH2:7][C:6]([OH:37])=[O:5])=[N:18][CH:17]=[N:16][C:15]=3[O:19][C:20]=2[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 58016826HCID 58016826, compound

Product 1

HCID 58016765HCID 58016765, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

Dissolve 45 mg (0.09 mmol) (3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}-2-methylpropoxy)acetic acid tert.-butyl ester (Enantiomer 2) in 0.5 ml dioxan, add 0.2 ml 4 N hydrogen chloride in dioxan and stir for 48 h at RT. Then add a further 0.4 ml 4 N hydrogen chloride in dioxan to the reaction mixture and stir again for 16 h at RT. After concentrating the reaction solution by evaporation under vacuum, purify the residue by preparative RP-HPLC (gradient: water/acetonitrile). 21 mg (53% of theor.) of the desired product is obtained as Enantiomer 2.

Workup

  1. stirringstir again for 16 h at RT
  2. concentrationAfter concentrating the reaction solution
  3. customby evaporation under vacuum
  4. custompurify the residue by preparative RP-HPLC (gradient: water/acetonitrile)

Sources & evidence

ORD record
ord-012e3ca00e034326b214de802ac8b457
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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