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Sodium Bicarbonate → Trifluoroacetic acid

HRID 475540
Notes
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Reaction equation

HRID 475540 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([C@H:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[CH2:14][NH2:15])[CH2:9]1)=O)(C)(C)C.[O:27]1[C:31]([C:32]2[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=2)=[CH:30][N:29]=[CH:28]1.[C:42](=[O:45])(O)[O-:43].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[O:27]1[C:31]([C:32]2[CH:33]=[CH:34][C:35]([S:38]([NH:15][CH2:14][C@H:13]([C@H:10]3[CH2:11][CH2:12][NH:8][CH2:9]3)[O:16][C:17]3[CH:18]=[CH:19][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=3)(=[O:40])=[O:39])=[CH:36][CH:37]=2)=[CH:30][N:29]=[CH:28]1.[C:42]([OH:43])([C:23]([F:26])([F:25])[F:24])=[O:45]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 27764154-(1,3-Oxazol-5-yl)benzenesulphonyl chlorideHCID 67776985(S)-3-[(S)-2-Amino-1-(4-trifluoromethylphenoxy)ethyl]pyrrolidine-1-carboxylic Acid t-Butyl Ester

Product 2

HCID 6422Trifluoroacetic acidHCID 677758584-Oxazol-5-yl-N-[(S)-2-(S)-pyrrolidin-3-yl-2-(4-trifluoromethylphenoxy)ethyl]benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

(S)-3-[(S)-2-Amino-1-(4-trifluoromethylphenoxy)ethyl]pyrrolidine-1-carboxylic acid t-butyl ester (35.0 mg, 0.093.5 mol, 1.0 eq.) was dissolved in DCM (1.2 mL) and triethylamine (39.1 μL). A solution of 4-(1,3-oxazol-5-yl)benzenesulfonyl chloride (56.9 mg, 234 μmol, 2.5 eq.) in DCM (0.4 mL,) was then added. The resulting mixture was stirred for 1 hour at room temperature. Saturated sodium bicarbonate was then added (1 mL) and the mixture was diluted with DCM (2 mL). The organic layer was collected and concentrated under reduced pressure. The crude material was redissolved in 1.2 M of HCl in EtOH (1.9 mL) and stirred at room temperature overnight. The mixture was then concentrated under reduced pressure then redissolved in 1:1 AcOH/H2O (1.5 mL) and purified by preparative HPLC to yield the title compound as a TFA salt (20.1 mg). MS m/z: [M+H]+ calcd for C22H22F3N3O4S, 482.13. found 482.4.

Workup

  1. customThe organic layer was collected
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe crude material was redissolved in 1.2 M of HCl in EtOH (1.9 mL)
  4. stirringstirred at room temperature overnight
  5. concentrationThe mixture was then concentrated under reduced pressure
  6. dissolutionthen redissolved in 1:1 AcOH/H2O (1.5 mL)
  7. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-644aed644df345d58fcac156f420d607
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08637568B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes