Hydrochloric Acid → HCID 58468264, compound

HRID 2094637Notes

Reaction equation

HRID 2094637 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]([F:39])=[CH:31][CH:30]=2)[C@@H:9]([C:13]2[CH:28]=[CH:27][C:16]([C:17]([NH:19][CH2:20][CH2:21][C:22]([O:24]CC)=[O:23])=[O:18])=[CH:15][CH:14]=2)[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.[Li+].[OH-].Cl>C(O)C.C1COCC1.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]([F:39])=[CH:31][CH:30]=2)[C@@H:9]([C:13]2[CH:28]=[CH:27][C:16]([C:17]([NH:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[O:18])=[CH:15][CH:14]=2)[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58468280HCID 58468280, compound

Product 1

HCID 58468264HCID 58468264, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl N-(4-{(1S)-1-[(4-chlorophenyl)(4-fluoro-1-naphthyl)methyl]butyl}benzoyl)-β-alaninate (160 mg, 0.293 mmol) in ethanol (2 mL) and THF (2 mL) was added LiOH (2.0 N in water, 2.93 mL, 5.86 mmol), then the mixture was stirred for one hour. The mixture was diluted with DCM, then acidified with 2.0 N HCl (aq). The layers were separated, then the organic layer was dried over MgSO4, filtered, then concentrated. The residue was purified by silica gel chromatography eluting with 10% MeOH/DCM to obtain the title compound as a white solid. 1H NMR (499 MHz, CD3OD): δ 8.40 (d, J=8.8 Hz, 1H); 7.92 (d, J=8.3 Hz, 1H); 7.70 (dd, J=8.2, 5.3 Hz, 1H); 7.60 (d, J=8.3 Hz, 2H); 7.55 (t, J=7.6 Hz, 1H); 7.50 (d, J=8.1 Hz, 2H); 7.45 (t, J=7.6 Hz, 1H); 7.39 (d, J=8.1 Hz, 2H); 7.30 (d, J=8.3 Hz, 2H); 7.00 (dd, J=10.4, 8.2 Hz, 1H); 5.19 (d, J=11.5 Hz, 1H); 3.52 (t, J=6.9 Hz, 2H); 3.36-330 (m, 1H); 2.53 (t, J=7.0 Hz, 2H); 1.62 (d, J=10.4 Hz, 2H); 1.11-1.05 (m, 2H); 0.78 (t, J=7.3 Hz, 3H). LC3 4.01 min. [M+H]+ 518.

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 10% MeOH/DCM

Sources & evidence

ORD record
ord-212a3339a95143a58ef183847e2d3df2
Source dataset
uspto-grants-2013_05
Patent number
US08445538B2

Reaction notes

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