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Sodium Hydroxide → 1-{2-[3-(2-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazol-5-yl)-5-fluoro-2-(methyloxy)phenyl]ethyl}-3-azetidinecarboxylic acid

HRID 1942740
Notes
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Reaction equation

HRID 1942740 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:13][C:14]([C:17]3[C:18]([O:34][CH3:35])=[C:19]([CH2:24][CH2:25][N:26]4[CH2:29][CH:28]([C:30]([O:32]C)=[O:31])[CH2:27]4)[CH:20]=[C:21]([F:23])[CH:22]=3)=[CH:15][N:16]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+]>C(O)(C)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:13][C:14]([C:17]3[C:18]([O:34][CH3:35])=[C:19]([CH2:24][CH2:25][N:26]4[CH2:29][CH:28]([C:30]([OH:32])=[O:31])[CH2:27]4)[CH:20]=[C:21]([F:23])[CH:22]=3)=[CH:15][N:16]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58494059Methyl 1-{2-[3-(2-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazol-5-yl)-5-fluoro-2-(methyloxy)phenyl]ethyl}-3-azetidinecarboxylate

Product 1

HCID 545767241-{2-[3-(2-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazol-5-yl)-5-fluoro-2-(methyloxy)phenyl]ethyl}-3-azetidinecarboxylic acidYield 21.6%

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
HCID 3776IsopropanolSolvent

Procedure

To a solution of methyl 1-{2-[3-(2-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazol-5-yl)-5-fluoro-2-(methyloxy)phenyl]ethyl}-3-azetidinecarboxylate (D82) (100 mg) in isopropanol (15 mL) and water (5 mL) stirred under nitrogen at room temperature was added 2 M NaOH (0.193 mL) in one charge. The reaction mixture was stirred at room temperature overnight. Isopropanol was removed in vacuo. The residue was dissolved in water and acidified with 1N HCl to pH=5. The solvent was removed in vacuo, the residue was dissolved in THF, and filtered. The filtrate was purified by Mass Directed AutoPrep to give 1-{2-[3-(2-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazol-5-yl)-5-fluoro-2-(methyloxy)phenyl]ethyl}-3-azetidinecarboxylic acid (E33) (21 mg) as a TFA salt. δH (DMSO-d6, 400 MHz): 1.34 (6H, d), 2.90 (2H, t), 3.47 (2H, br. s.), 3.66 (4H, m), 4.28 (4H, m), 4.80 (1H, m), 7.26 (1H, d), 7.32 (1H, d), 7.73 (1H, dd), 7.90 (1H, dd), 8.01 (1H, d), 8.46 (1H, s), 10.12 (1H, br s), 13.13 (1H, br s). δF (DMSO-d6, 376 MHz): −117.4, −73.9. MS (ES): C25H26ClFN2O4S requires 504. found 505.2 (M+H+).

Workup

  1. additioncharge
  2. customIsopropanol was removed in vacuo
  3. dissolutionThe residue was dissolved in water
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residue was dissolved in THF
  6. filtrationfiltered
  7. customThe filtrate was purified by Mass Directed AutoPrep

Sources & evidence

ORD record
ord-6046aa5031a34120b968f10685c2b78d
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08389508B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes