Acetic Acid → HCID 44365865, compound

HRID 1292391Notes

Reaction equation

HRID 1292391 reaction equation
C(OC([N:11]([CH2:38][CH2:39][CH2:40][CH2:41][C:42]1[CH:47]=[CH:46][C:45]([O:48]CC2C=CC=CC=2)=[CH:44][CH:43]=1)[CH2:12][CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][C:24](=[O:29])[NH:25][CH2:26][CH2:27][CH3:28])[CH:21]=2)[NH:16][C:15]=1[C:30]1[CH:35]=[C:34]([CH3:36])[CH:33]=[C:32]([CH3:37])[CH:31]=1)=O)C1C=CC=CC=1.C(O)(=O)C.[H][H]>O1CCCC1.CO.[Pd].O>[CH3:36][C:34]1[CH:35]=[C:30]([C:15]2[NH:16][C:17]3[C:22]([C:14]=2[CH2:13][CH2:12][NH:11][CH2:38][CH2:39][CH2:40][CH2:41][C:42]2[CH:43]=[CH:44][C:45]([OH:48])=[CH:46][CH:47]=2)=[CH:21][C:20]([O:23][C:24](=[O:29])[NH:25][CH2:26][CH2:27][CH3:28])=[CH:19][CH:18]=3)[CH:31]=[C:32]([CH3:37])[CH:33]=1

Participants

8

Reactant 3

HCID 176Acetic AcidHCID 53951440HCID 53951440, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 44365865HCID 44365865, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of propylcarbamic acid 3-(2-[benzyloxycarbonyl-[4-(4-benzyloxyphenyl)butyl]amino]-ethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl ester (17 mg in a mixture of 1.5 mL tetrahydrofuran and 0.5 mL methanol) was added 16 mg of 10% palladium on carbon catalyst followed by acetic acid (0.010 mL of a 30% solution in water). The reaction flask was fitted with a hydrogen balloon, evacuated and recharged with hydrogen (3 times) and stirred at room temperature. After 1.5 hours the reaction was flushed with nitrogen, filtered over diatomaceous earth and concentrated in vacuo. Purification by flash chromatography (methylene chloride:methanol:ammonium hydroxide, 90:6:1) gave the title compound (11 mg). m/e=514 (M+H)

Workup

  1. customevacuated
  2. customAfter 1.5 hours the reaction was flushed with nitrogen
  3. filtrationfiltered over diatomaceous earth
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (methylene chloride:methanol:ammonium hydroxide, 90:6:1)

Sources & evidence

ORD record
ord-fe1822ff46894bd0a8c13444d9021fb8
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

Loading…