m-Chloroperbenzoic acid → HCID 59174893, compound

HRID 1177436Notes

Reaction equation

HRID 1177436 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:26][N:27]2[CH2:30][CH:29]([C:31]([OH:33])=[O:32])[CH2:28]2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.C1C=C(Cl)C=C(C(OO)=[O:42])C=1>CO.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH2:26][N+:27]2([O-:42])[CH2:28][CH:29]([C:31]([OH:33])=[O:32])[CH2:30]2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 44600476HCID 44600476, compound

Product 1

HCID 59174893HCID 59174893, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A slurry of 1-((3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)-phenyl)methyl)azetidine-3-carboxylic acid (0.084 g, 0.18 mmol) and mCPBA (0.063 g, 0.37 mmol) in 5 mL 10% MeOH/DCM was stirred rapidly at ambient temperature. After about 10 min, the reaction mixture became clear. After 10 additional minutes precipitates formed. After 10 additional minutes, the reaction mixture was filtered, rinsing with DCM. The solid was collected and dried in vacuo to give 1-((3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)azetidine-3-carboxylic acid N-oxide as a mixture of isomers. The isomers were separated by RPHPLC (A=0.2% formic acid in water; B=0.04% formic acid in acetonitirle; 30×100, Gemini Axia, Sum) to give (1r,3s)-3-carboxy-1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzyl)azetidine 1-oxide and (1s,3r)-3-carboxy-1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzyl)azetidine 1-oxide. MS (ESI) m/z: Calculated: 475.1; Observed: 476.1 (M++1).

Workup

  1. customAfter 10 additional minutes precipitates
  2. customformed
  3. filtrationAfter 10 additional minutes, the reaction mixture was filtered
  4. washrinsing with DCM
  5. customThe solid was collected
  6. customdried in vacuo

Sources & evidence

ORD record
ord-5b49f484f93341c583dd6450dd23a790
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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