Hydrochloric Acid → (1-{4-Cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}azetidin-3-yl)acetic Acid

HRID 17480Notes

Reaction equation

HRID 17480 reaction equation
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([N:12]3[CH2:15][CH:14]([CH2:16][C:17]([O:19]CC)=[O:18])[CH2:13]3)[O:11][C:7]=2[C:6]([N:22]2[CH2:26][CH2:25][C@H:24]([N:27]([CH3:29])[CH3:28])[CH2:23]2)=[C:5]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:4]=1[CH3:36])#[N:2].[OH-].[Na+].Cl>O1CCCC1>[C:1]([C:3]1[C:8]2[N:9]=[C:10]([N:12]3[CH2:15][CH:14]([CH2:16][C:17]([OH:19])=[O:18])[CH2:13]3)[O:11][C:7]=2[C:6]([N:22]2[CH2:26][CH2:25][C@H:24]([N:27]([CH3:29])[CH3:28])[CH2:23]2)=[C:5]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:4]=1[CH3:36])#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86630853HCID 86630853, compound

Product 1

HCID 68584433(1-{4-Cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}azetidin-3-yl)acetic AcidYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (1-{4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}azetidin-3-yl)acetate (I-191) (220 mg, 0.45 mmol) was dissolved in tetrahydrofuran (5 ml), then 1 N sodium hydroxide (4.5 ml, 4.5 mmol) was added, followed by stirring at room temperature for 18 hours. After the reaction, the solvent was evaporated away under reduced pressure, then 1 N hydrochloric acid (4.5 ml, 4.5 mmol) was added, followed by extraction with a mixed solvent of chloroform:methanol (10:1) and by washing with saturated sodium hydrogencarbonate solution, then the organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was subjected to preparative silica gel column chromatography. The eluate with chloroform/methanol (4:1, v/v) gave the entitled compound (35 mg, 17%) as a pale yellow crystal.

Workup

  1. customAfter the reaction
  2. customthe solvent was evaporated away under reduced pressure
  3. extractionfollowed by extraction with a mixed solvent of chloroform:methanol (10:1)
  4. washby washing with saturated sodium hydrogencarbonate solution
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-1ec25370eb004dbea18ad7260458b590
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

Loading…