Trifluoroacetic acid → HCID 11513092, compound

HRID 2378115Notes

Reaction equation

HRID 2378115 reaction equation
FC(F)(F)C(O)=O.[CH:8]([O:11][C:12]([N:14]1[C:23]2[C:18](=[N:19][C:20]([C:24]([F:27])([F:26])[F:25])=[CH:21][CH:22]=2)[C@H:17]([N:28]([CH2:44][C:45]2[CH:50]=[C:49]([C:51]([F:54])([F:53])[F:52])[CH:48]=[C:47]([C:55]([F:58])([F:57])[F:56])[CH:46]=2)[C:29]2[N:30]=[N:31][N:32]([CH2:34][CH2:35][NH:36]C(OC(C)(C)C)=O)[N:33]=2)[CH2:16][C@@H:15]1[CH2:59][CH3:60])=[O:13])([CH3:10])[CH3:9].C(=O)(O)[O-].[Na+]>ClCCl>[CH:8]([O:11][C:12]([N:14]1[C:23]2[C:18](=[N:19][C:20]([C:24]([F:27])([F:25])[F:26])=[CH:21][CH:22]=2)[C@H:17]([N:28]([C:29]2[N:30]=[N:31][N:32]([CH2:34][CH2:35][NH2:36])[N:33]=2)[CH2:44][C:45]2[CH:46]=[C:47]([C:55]([F:56])([F:57])[F:58])[CH:48]=[C:49]([C:51]([F:52])([F:53])[F:54])[CH:50]=2)[CH2:16][C@@H:15]1[CH2:59][CH3:60])=[O:13])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86613795HCID 86613795, compound

Product 1

HCID 11513092HCID 11513092, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic acid (1 mL) to a solution of (+/−)-cis-4-[(3,5-bis-trifluoromethyl-benzyl)-[2-(2-tert-butoxycarbonylamino-ethyl)-2H-tetrazol-5-yl)-amino]-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid isopropyl ester (61 mg, 0.079 mmol) in dichloromethane (3 mL) and stir the mixture at room temperature for 3 h. Pour the reaction mixture onto a saturated solution of sodium bicarbonate and extract with dichloromethane. Dry the organic layer over anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure. Purify the residue by silica gel chromatography, eluting with ethyl acetate, to afford the title compound (24 mg, 45%). MS (ES+): 669 (M+H).

Workup

  1. extractionextract with dichloromethane
  2. dry with materialDry the organic layer over anhydrous sodium sulfate
  3. filtrationfilter
  4. customremove the solvent under reduced pressure
  5. customPurify the residue by silica gel chromatography
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-821e9feb36554be1a47510b3f314e971
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

Loading…