Sodium Hydroxide → HCID 54767838, compound

HRID 1503280Notes

Reaction equation

HRID 1503280 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:32])[CH:7]([NH2:31])[CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)[CH:16]=2)[NH:11][CH:10]=1)C>CO>[NH2:31][CH:7]([CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)[CH:16]=2)[NH:11][CH:10]=1)[C:6]([OH:32])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54767996HCID 54767996, compound

Product 1

HCID 54767838HCID 54767838, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

2-Amino-3-[5-(4-phenoxyphenyl)-1H-indol-3-yl]propionic acid (9) was prepared as follows: NaOH (2N aqueous, 1 mL) was added to a solution of compound 7 prepared in Example 1 (0.2 g) in MeOH (4 mL) at 0° C. The reaction mixture was shaken at 30° C. for 24 hours. The solvents were evaporated under vacuum. The residues were dissolved in CHCl3 (40 mL) and neutralized to pH ˜2 with 1N HCl aqueous. The organic layer was separated, washed with brine and concentrated to get a sticky oil, which was washed with Et2O, and dried under vacuum to afford compound 9 as a HCl-salt (white solid, 7 0 mg, 35%): 1H-NMR (400 MHz, CD3OD) δ: 7.88 (s, 1H), 7.58-7.72 (m, 2H), 7.25-7.41 (m, 4H), 6.88-7.05 (m, 5H), 3.47-3.72 (m, 1H), 3.25-3.28 (m, 1H), 2.81-2.88 (m, 1H); LC/MS: m/z=358 [M+H]+ (Calc: 372.4).

Workup

  1. custom2-Amino-3-[5-(4-phenoxyphenyl)-1H-indol-3-yl]propionic acid (9) was prepared
  2. customThe solvents were evaporated under vacuum
  3. dissolutionThe residues were dissolved in CHCl3 (40 mL)
  4. customThe organic layer was separated
  5. washwashed with brine
  6. concentrationconcentrated
  7. customto get a sticky oil, which
  8. washwas washed with Et2O
  9. customdried under vacuum

Sources & evidence

ORD record
ord-704cdb5daf994f339535d97b49ecafc7
Source dataset
uspto-grants-2015_12
Patent number
US09212139B2

Reaction notes

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