HCID 70560825, compound → HCID 70565237, compound

HRID 1477849Notes

Reaction equation

HRID 1477849 reaction equation
C(OC([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:18]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)([CH2:23][CH3:24])[C:19]([O:21][CH3:22])=[O:20])=O)(C)(C)C>Cl.CO>[NH2:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:18]([C:25]1[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=1)([CH2:23][CH3:24])[C:19]([O:21][CH3:22])=[O:20]

Participants

3

Reactant 1

HCID 70560825HCID 70560825, compound

Product 1

HCID 70565237HCID 70565237, compound

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

A mixture of methyl 2-(4-(tert-butoxycarbonylamino)-1H-indol-1-yl)-2-(4-chlorophenyl)butanoate (500 mg), as described in Example 3 Step A, in 10 mL of 4 N HCl/MeOH was stirred at room temperature for 1 h. Then the solvent was removed. The residue was dissolved in EA (30 mL) and pH value was adjusted to 9˜10 with saturated aq. NaHCO3. The organic layers was washed with water (10 mL), brine, dried over sodium sulfate and concentrated to give the title product as a pale brown solid. LC/MS m/z=343.2 [M+H]+.

Workup

  1. customThen the solvent was removed
  2. dissolutionThe residue was dissolved in EA (30 mL)
  3. washThe organic layers was washed with water (10 mL), brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-388467ea1a624c76b0790f032a0af0cc
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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