Hydrochloric Acid → HCID 12971978, compound

HRID 989906Notes

Reaction equation

HRID 989906 reaction equation
[C:1]1([CH:7]([CH2:14][C:15]2[O:16][CH:17]=[C:18]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[N:19]=2)[CH2:8][C:9]([O:11]CC)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH-].Cl>C1COCC1.O>[C:1]1([CH:7]([CH2:14][C:15]2[O:16][CH:17]=[C:18]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[N:19]=2)[CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 23389061HCID 23389061, compound

Product 1

HCID 12971978HCID 12971978, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of ethyl (±)-3-phenyl-4-[4-[5-(pyridin-2-yl)amino- 1-pentyl]-1,3-oxazol-2-yl]butanoate (75 mg, 0.18 mmole) in 1:1 THF/H2O (2 mL) was added 1.0 N LiOH (0.27 mL, 0.27 mmole). After 18 hr, the pH was adjusted to 6 using 10% HCl; then the solution was concentrated under reduced pressure to remove the THF. The solution was chromatographed on a C-18 Mega Bond Elut® column (50 mL H2O then 200 mL 20% CH3CN/H2O containing 0.1% TFA). Fractions containing the product were pooled and lyophilized to give the title compound (43 mg, 61%) as a yellow gum: MS (ES) m/e 394 (M+H)+. Anal. Calcd for C23H27N3O3.0.098 CF3CO2H: C, 68.85; H, 6.75; N, 10.38. Found: C, 69.23; H, 7.00; N, 9.98.

Workup

  1. concentrationthen the solution was concentrated under reduced pressure
  2. customto remove the THF
  3. customThe solution was chromatographed on a C-18 Mega Bond Elut® column (50 mL H2O
  4. additionFractions containing the product

Sources & evidence

ORD record
ord-2939039364d2495aafd4f4c7f59f7592
Source dataset
uspto-grants-2002_10
Patent number
US06458814B1

Reaction notes

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