Trifluoroacetic acid → Trifluoroacetic acid

HRID 857735Notes

Reaction equation

HRID 857735 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[Cl:8][C:9]1[CH:10]=[C:11]([C:15]([OH:44])([C:38]2[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=2)[C:16]([N:18]2[CH2:37][CH2:36][CH2:35][C@H:19]2[C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[N:30]2[CH:34]=[N:33][N:32]=[N:31]2)=[O:21])=[O:17])[CH:12]=[CH:13][CH:14]=1.C(=O)(O)[O-:46].[Na+].ClC1C=C(C=CC=1)C(OO)=O>ClCCl.CCOC(C)=O>[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[Cl:8][C:9]1[CH:10]=[C:11]([C:15]([OH:44])([C:38]2[CH:39]=[N+:40]([O-:46])[CH:41]=[CH:42][CH:43]=2)[C:16]([N:18]2[CH2:37][CH2:36][CH2:35][C@H:19]2[C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[N:30]2[CH:34]=[N:33][N:32]=[N:31]2)=[O:21])=[O:17])[CH:12]=[CH:13][CH:14]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 58760146HCID 58760146, compound2×

Product 2

HCID 6422Trifluoroacetic acidHCID 58760172HCID 58760172, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The TFA salt of the polar isomer of 1-[(3-chlorophenyl)(hydroxy)pyridin-3-ylacetyl]-N-[2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide (0.01 g, 0.02 mmol) was partitioned between EtOAc and saturated sodium bicarbonate solution and extracted with EtOAc to retrieve the free base. To a stirred solution of the dried free base of 1-[(3-chlorophenyl)(hydroxy)pyridin-3-ylacetyl]-N-[2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide (0.009 g, 0.017 mmol) in dichloromethane (1 mL), cooled to 0° C., was added 3-chloroperoxybenzoic acid 70% (0.006 g, 0.026 mmol). After 2 hours, the reaction was evaporated in vacuo and purified on a Gilson Preparative HPLC. Pure fractions were combined, freeze dried and lyophilized to yield the solid TFA salt of 1-[(3-chlorophenyl)(hydroxy)(1-oxidopyridin-3-yl)acetyl]-N-[2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide (0.003 g, HPLC RT=2.70 min, Method A; LCMS m/z=534).

Workup

  1. extractionextracted with EtOAc
  2. customthe reaction was evaporated in vacuo
  3. custompurified on a Gilson Preparative HPLC
  4. customfreeze dried

Sources & evidence

ORD record
ord-296b621786634fbbb500fc059187521f
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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