Lithium Hydroxide → HCID 9953998, compound

HRID 989905Notes

Reaction equation

HRID 989905 reaction equation
[C:1]1([CH:7]([CH2:14][C:15]2[O:16][CH:17]=[C:18]([C:20]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)=[O:21])[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-]>C1COCC1.O>[C:1]1([CH:7]([CH2:14][C:15]2[O:16][CH:17]=[C:18]([C:20]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)=[O:21])[N:19]=2)[CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86758538HCID 86758538, compound

Product 1

HCID 9953998HCID 9953998, compoundYield 83%

Reagents, catalysts & solvents 1

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

Procedure

To a solution of ethyl (±)-3-phenyl-4-[4-[[[4-(pyridin-2-yl)amino-1-butyl]amino]carbonyl]-1,3-oxazol-2-yl]butanoate (197 mg, 0.44 mmole) in 1:1 THF/H2O (4 mL) was added 1.0 N LiOH (0.66 mL, 0.66 mmole). After 24 hr, the mixture was washed with Et2O (2×2 mL), and the pH of the aqueous layer was adjusted to 6 using 10% HCl. The solution was chromatographed on a C-18 Mega Bond Elut® column (50 mL H2O then 50 mL 20% CH3CN/H2O). Fractions containing the product were pooled and lyophilized to give the title compound (154 mg, 83%) as a white powder: MS (ES) m/e 423 (M+H)+. Anal. Calcd for C23H26N4O4.0.75 H2O: C, 63.36; H, 6.36; N, 12.85. Found: C, 63.55; H, 6.27; N, 12.50.

Workup

  1. washthe mixture was washed with Et2O (2×2 mL)
  2. customThe solution was chromatographed on a C-18 Mega Bond Elut® column (50 mL H2O
  3. additionFractions containing the product

Sources & evidence

ORD record
ord-6fc5723be0514614adacc9539e633896
Source dataset
uspto-grants-2002_10
Patent number
US06458814B1

Reaction notes

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