Lithium Hydroxide → HCID 9865410, compound

HRID 989904Notes

Reaction equation

HRID 989904 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][NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=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][NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=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 86758537HCID 86758537, compound

Product 1

HCID 9865410HCID 9865410, compoundYield 33%

Reagents, catalysts & solvents 1

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

Procedure

To a solution of ethyl(±)-3-phenyl-4-[4-[[[2-(pyridin-2-yl)amino-1-ethyl]amino]carbonyl]-1,3-oxazol-2-yl]butanoate (157 mg, 0.37 mmole) in 1:1 THF/H2O (4 mL) was added 1.0 N LiOH (0.56 mL, 0.56 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 10% CH3CN/H2O). Fractions containing the product were pooled and lyophilized to give the title compound (48 mg, 33%) as a white powder: MS (ES) m/e 395 (M+H)+. Anal. Calcd for C21H22N4O4. 0.75 HCl: C, 59.80; H, 5.44; N, 13.28. Found: C, 59.89; H, 5.50; N, 12.98.

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-7121495e481e40e887196c6d46666f99
Source dataset
uspto-grants-2002_10
Patent number
US06458814B1

Reaction notes

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