1-bromo-3-methylnaphthalene → HCID 58468276, compound

HRID 2094642Notes

Reaction equation

HRID 2094642 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8](O)[C@@H:9]([C:13]2[CH:28]=[CH:27][C:16]([C:17]([NH:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:18])=[CH:15][CH:14]=2)[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.[Br:30][C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[C:33]([CH3:41])[CH:32]=1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:36]2[C:35]3[C:40](=[C:31]([Br:30])[CH:32]=[C:33]([CH3:41])[CH:34]=3)[CH:39]=[CH:38][CH:37]=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][CH2:25][CH3:26])=[O:23])=[O:18])=[CH:15][CH:14]=2)[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2991271-bromo-3-methylnaphthaleneHCID 58468263HCID 58468263, compound

Product 1

HCID 58468276HCID 58468276, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trifluoroacetic acid (50 mL) was added to ethyl N-(4-{(1R)-1-[(R)-(4-chlorophenyl)(hydroxy)methyl]butyl}benzoyl)-β-alaninate (EXAMPLE 1, Step A, 2.00 g, 4.79 mmol) and 1-bromo-3-methylnaphthalene (1.16 g, 5.26 mmol). The solution was stirred overnight at RT, then the solvent was evaporated and the residue was purified by silica gel chromatography eluting with 0-15% EtOAc/hexanes to afford the title compound. LC3 4.49 min. [M+H]+ 622.

Workup

  1. customthe solvent was evaporated
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with 0-15% EtOAc/hexanes

Sources & evidence

ORD record
ord-e2086a4ba4ce4d4fb27aec9ff908503a
Source dataset
uspto-grants-2013_05
Patent number
US08445538B2

Reaction notes

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