Potassium Carbonate → tert-Butyl 3-(4-(tert-Butoxycarbonylamino)-1H-indol-1-yl)-3-(4-chlorophenyl)pent-4-ynoate

HRID 1427289Notes

Reaction equation

HRID 1427289 reaction equation
[C:1]([O:5][C:6]([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:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)([CH:27]=O)[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:36]([O-])([O-])=O.[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO>[C:1]([O:5][C:6]([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:29]1[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=1)([C:27]#[CH:36])[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 86705057tert-butyl 3-(4-(tert-butoxycarbonylamino)-1H-indol-1-yl)-3-(4-chlorophenyl)-4-oxobutanoateHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 86705058tert-Butyl 3-(4-(tert-Butoxycarbonylamino)-1H-indol-1-yl)-3-(4-chlorophenyl)pent-4-ynoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the product of Step D (750 mg, 1.5 mmol) in MeOH (10 mL) was added K2CO3 (414 mg, 3 mmol) and dimethyl 1-diazo-2-oxopropylphosphonate (576 mg, 3 mmol). The mixture was stirred at room temperature for 2 h. After removing the organic solvent, the residue was added H2O (10 mL), extracted with ethyl acetate, and washed with brine (10 mL), dried over sodium sulfate, then filtered. The solvent was evaporated in vacuo, and the residue was purified by silica gel chromatography (EA/PE=1:8) to obtain the title compound as colorless solid. LC/MS m/z=495.2[M+H]+.

Workup

  1. customAfter removing the organic solvent
  2. additionthe residue was added H2O (10 mL)
  3. extractionextracted with ethyl acetate
  4. washwashed with brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated in vacuo
  8. customthe residue was purified by silica gel chromatography (EA/PE=1:8)

Sources & evidence

ORD record
ord-0e267e5764674bd4b2de006f63d14ba3
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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