Hydrochloric Acid → benzyl 4-[3-[3-(N-benzyl-N-tert-butoxycarbonylamino)benzoyl]indol-1-yl]butyrate

HRID 249178Notes

Reaction equation

HRID 249178 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]1[CH:12]=[C:13]([CH:31]=[CH:32][CH:33]=1)[C:14]([C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH:17]=1)=[O:15])=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.Cl>CN(C)C=O>[CH2:34]([N:10]([C:11]1[CH:12]=[C:13]([CH:31]=[CH:32][CH:33]=1)[C:14]([C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:14][C:13]2[CH:31]=[CH:32][CH:33]=[CH:11][CH:12]=2)=[O:29])[CH:17]=1)=[O:15])[C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 190247254-[3-(3-Tert-butoxycarbonylaminobenzoyl)indol-1-yl]butyric acid

Product 1

HCID 19024831benzyl 4-[3-[3-(N-benzyl-N-tert-butoxycarbonylamino)benzoyl]indol-1-yl]butyrateYield 96.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

60% Sodium hydride in mineral oil (0.13 g) was added to a solution of 4-[3-(3-tert-butoxycarbonylaminobenzoyl)indol-1-yl]butyric acid (0.47 g) in N,N-dimethylformamide (7 ml). The mixture was stirred at 0° C. for 1 hour. Benzyl bromide (0.95 g) was added to the mixture and the ixture was stirred at room temperature for 20 hours. The mixture was poured into ice water and 0.5N-hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (30 g) eluting with a mixture of n-hexane and ethyl acetate (5:1) to give benzyl 4-[3-[3-(N-benzyl-N-tert-butoxycarbonylamino)benzoyl]indol-1-yl]butyrate (325 mg) as an oil.

Workup

  1. stirringthe ixture was stirred at room temperature for 20 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (30 g)
  7. washeluting with a mixture of n-hexane and ethyl acetate (5:1)

Sources & evidence

ORD record
ord-44c45fc83b574a23a0d4d17f24fd0b31
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Reaction notes

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