Hydrochloric Acid → HCID 11563853, compound

HRID 2378120Notes

Reaction equation

HRID 2378120 reaction equation
[Li+].[OH-].C[O:4][C:5]([C:7]([CH3:51])([CH3:50])[CH2:8][O:9][C:10]([N:12]1[C:21]2[C:16](=[N:17][C:18]([C:22]([F:25])([F:24])[F:23])=[CH:19][CH:20]=2)[C@@H:15]([N:26]([CH2:33][C:34]2[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:37]=[C:36]([C:44]([F:47])([F:46])[F:45])[CH:35]=2)[C:27]2[N:28]=[N:29][N:30]([CH3:32])[N:31]=2)[CH2:14][C@H:13]1[CH2:48][CH3:49])=[O:11])=[O:6].Cl>C1COCC1>[C:5]([C:7]([CH3:50])([CH3:51])[CH2:8][O:9][C:10]([N:12]1[C:21]2[C:16](=[N:17][C:18]([C:22]([F:25])([F:24])[F:23])=[CH:19][CH:20]=2)[C@@H:15]([N:26]([CH2:33][C:34]2[CH:35]=[C:36]([C:44]([F:47])([F:45])[F:46])[CH:37]=[C:38]([C:40]([F:41])([F:42])[F:43])[CH:39]=2)[C:27]2[N:28]=[N:29][N:30]([CH3:32])[N:31]=2)[CH2:14][C@H:13]1[CH2:48][CH3:49])=[O:11])([OH:6])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 11563885HCID 11563885, compound

Product 1

HCID 11563853HCID 11563853, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add LiOH 2.5 M (1.9 mL, 4.8 mmol) to a solution of (2R,4S)-4-[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid 2-methoxycarbonyl-2-methyl-propyl ester (74 mg, 0.10 mmol) in THF (1.9 mL). Stir the mixture at room temperature for 72 h. Acidify with 1 M HCl. Extract the aqueous phase with dichloromethane. Dry the organic layers over Na2SO4, filter, and concentrate. Purify the residue using silica gel chromatography (elution with hexane/ethyl acetate) to afford the title compound (14 mg, 20%). MS (ES+): 698 (M+H).

Workup

  1. extractionExtract the aqueous phase with dichloromethane
  2. dry with materialDry the organic layers over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the residue
  6. washsilica gel chromatography (elution with hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b4825f68d4da40188e0e9369e57d728e
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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