Hydrochloric Acid → HCID 46829693, compound

HRID 2094648Notes

Reaction equation

HRID 2094648 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]([C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)[C@@H:13]([C:17]2[CH:32]=[CH:31][C:20]([C:21]([NH:23][CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])=[O:22])=[CH:19][CH:18]=2)[CH2:14][CH2:15][CH3:16])=[CH:4][CH:3]=1.[Li+].[OH-].Cl>C(O)C.C(Cl)Cl>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]([C:33]2[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=2)[C@@H:13]([C:17]2[CH:32]=[CH:31][C:20]([C:21]([NH:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:22])=[CH:19][CH:18]=2)[CH2:14][CH2:15][CH3:16])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58468274HCID 58468274, compound

Product 1

HCID 46829693HCID 46829693, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl N-(4-{(1S)-1-[(4-fluoro-1-naphthyl)(4-methoxyphenyl)methyl]butyl}benzoyl)-β-alaninate (slower-eluting diastereomer, 10 mg, 0.018 mmol) in ethanol (2 mL) was added LiOH (2.0 N in water, 0.5 mL, 1.0 mmol), then the reaction mixture was stirred for one hour. The mixture was diluted with DCM (20 mL) acidified with 2.0 N HCl (aq). The organic layer was dried over MgSO4, concentrated, then the residue was purified by silica gel chromatography eluting with 10% MeOH/DCM to afford the title compound. 1H NMR (499 MHz, CDCl3): δ 8.27 (d, J=8.5 Hz, 1H); 8.13 (d, J=8.2 Hz, 1H); 7.67-7.49 (m, 5H); 7.20 (m, 3H); 6.95 (dd, J=8.3, 2.5 Hz, 2H); 6.76 (m, 1H); 6.51 (d, J=8.3 Hz, 2H); 4.86 (d, J=11.3 Hz, 1H); 3.76 (m, 2H); 3.60 (s, 3H); 3.58 (m, 1H); 2.65 (t, J=5.8 Hz, 2H); 1.70 (m, 2H); 1.07 (m, 2H); 0.76 (t, J=7.2 Hz, 3H). LC1 1.19 min. [M+]+ 514.

Workup

  1. dry with materialThe organic layer was dried over MgSO4
  2. concentrationconcentrated
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with 10% MeOH/DCM

Sources & evidence

ORD record
ord-1e032949cbd5439eb1c3b6d8d6398201
Source dataset
uspto-grants-2013_05
Patent number
US08445538B2

Reaction notes

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