Sodium Hydroxide → HCID 67265368, compound

HRID 1686001Notes

Reaction equation

HRID 1686001 reaction equation
C1([O:6][C:7](=[O:48])[C@@H:8]([NH:40][C:41](OC(C)(C)C)=[O:42])[CH2:9][CH2:10][O:11][C:12]2[CH:21]=[C:20]3[C:15]([C:16]([O:22][C:23]4[CH:28]=[CH:27][C:26]([NH:29][C:30](=O)[C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[CH:25][CH:24]=4)=[CH:17][CH:18]=[N:19]3)=[CH:14][C:13]=2[O:38][CH3:39])CCCC1.[OH-:49].[Na+]>C1COCC1>[C:30]([NH:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][C:16]2[C:15]3[C:20](=[CH:21][C:12]([O:11][CH2:10][CH2:9][C@H:8]([NH:40][C:41]([C:15]([CH3:20])([CH3:16])[CH3:14])=[O:42])[C:7]([OH:6])=[O:48])=[C:13]([O:38][CH3:39])[CH:14]=3)[N:19]=[CH:18][CH:17]=2)=[CH:24][CH:25]=1)(=[O:49])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 57699874HCID 57699874, compound

Product 1

HCID 67265368HCID 67265368, compoundYield 241.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-4-[4-(4-benzoylamino-phenoxy)-6-methoxy-quinolin-7-yloxy]-2-tert-butoxycarbonylamino-butyric acid cyclopentyl ester (17 mg, 0.02 mmol) in THF (1 ml) was added 2M NaOH (0.026 ml, 0.046 mmol, 2 eq). After 16 hours reaction was incomplete so an additional 2 equivalents of NaOH was added. The reaction was completed after 6 hours and the THF was removed under reduced pressure. The aqueous layer was diluted with 3 ml of water and acidified to pH 6 with 1M HCl. The title compound was extracted into ethyl acetate, dried over magnesium sulphate and isolated as a white solid (13.8 mg, 91% yield).

Workup

  1. customAfter 16 hours reaction
  2. additionwas added
  3. customthe THF was removed under reduced pressure
  4. additionThe aqueous layer was diluted with 3 ml of water
  5. extractionThe title compound was extracted into ethyl acetate
  6. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-fd68818432d74a6e8c3d593dec2adc14
Source dataset
uspto-grants-2012_04
Patent number
US08148531B2

Reaction notes

Loading…