Hydrochloric Acid → HCID 46829798, compound

HRID 2094639Notes

Reaction equation

HRID 2094639 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[C:34]([O:39][CH3:40])[CH:35]=3)[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.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[C:34]([O:39][CH3:40])[CH:35]=3)[CH:30]=2)[C@@H:9]([C:13]2[CH:14]=[CH:15][C:16]([C:17]([NH:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[O:18])=[CH:27][CH:28]=2)[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67438208HCID 67438208, compound

Product 1

HCID 46829798HCID 46829798, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl N-(4-{(1S)-1-[(4-chlorophenyl)(6-methoxy-2-naphthyl)methyl]butyl}benzoyl)-β-alaninate (4.0 mg, 0.0072 mmol) in ethanol (1 mL) was added LiOH (2.0 N in water, 0.1 mL, 0.2 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 (600 MHz, CD3OD): δ 7.53-7.48 (m, 6H); 7.42 (d, J=8.5 Hz, 1H); 7.33-7.28 (m, 5H); 6.98-6.94 (m, 2H); 5.47 (s, 1H); 4.32 (d, J=11.7 Hz, 1H); 3.79 (s, 3H); 3.51-3.47 (m, 2H); 2.50 (s, 2H); 1.56 (t, J=7.6 Hz, 2H); 1.04 (d, J=9.5 Hz, 2H); 0.73 (t, J=7.3 Hz, 3H); LC3 2.61 min. [M+H]+ 531.

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-019b420b68dd4a588eb9895581ec316a
Source dataset
uspto-grants-2013_05
Patent number
US08445538B2

Reaction notes

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