Hydrochloric Acid → HCID 58016795, compound

HRID 1926970Notes

Reaction equation

HRID 1926970 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:38])[CH2:6][CH2:7][CH2:8][N:9]([CH2:11][C@H:12]([O:14][C:15]1[C:16]2[C:23]([C:24]3[CH:29]=[CH:28][C:27]([CH2:30][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])[CH3:10].Cl>O1CCOCC1>[CH2:30]([C:27]1[CH:26]=[CH:25][C:24]([C:23]2[C:16]3[C:15]([O:14][C@H:12]([CH3:13])[CH2:11][N:9]([CH3:10])[CH2:8][CH2:7][CH2:6][C:5]([OH:38])=[O:4])=[N:20][CH:19]=[N:18][C:17]=3[O:21][C:22]=2[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:29][CH:28]=1)[CH3:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25096413HCID 25096413, compound

Product 1

HCID 58016795HCID 58016795, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Add 0.6 ml 1 N sodium hydroxide solution to a solution of 100 mg (73% purity, 0.15 mmol) 4-{[(2R)-2-{[5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}propyl](methyl)amino}butyric acid methyl ester in 3 ml dioxan, and stir for 16 h at RT. After adding 0.7 ml 1 N hydrochloric acid, extract with ethyl acetate. Re-extract the aqueous phase twice more with ethyl acetate. Combine the organic phases, dry over sodium sulphate, and filter. Concentrate the filtrate by vacuum evaporation. Take up the oily residue in acetonitrile and purify by preparative RP-HPLC (gradient: water/acetonitrile). 57 mg (80% of theor.) of the desired product is obtained.

Workup

  1. extractionextract with ethyl acetate
  2. dry with materialdry over sodium sulphate
  3. filtrationfilter
  4. concentrationConcentrate the filtrate
  5. customby vacuum evaporation
  6. custompurify by preparative RP-HPLC (gradient: water/acetonitrile)

Sources & evidence

ORD record
ord-e439a19a4546407a919a16c5b8019b8f
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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