Acetic Acid → HCID 44365793, compound

HRID 1292394Notes

Reaction equation

HRID 1292394 reaction equation
C(OC([N:11]([CH2:37][CH2:38][CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][C:44]([O:47]CC2C=CC=CC=2)=[CH:43][CH:42]=1)[CH2:12][CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][C:24](=[O:28])[NH:25][CH2:26][CH3:27])[CH:21]=2)[NH:16][C:15]=1[C:29]1[CH:34]=[C:33]([CH3:35])[CH:32]=[C:31]([CH3:36])[CH:30]=1)=O)C1C=CC=CC=1.C(O)(=O)C.[H][H]>O1CCCC1.CO.[OH-].[OH-].[Pd+2].O>[CH3:35][C:33]1[CH:34]=[C:29]([C:15]2[NH:16][C:17]3[C:22]([C:14]=2[CH2:13][CH2:12][NH:11][CH2:37][CH2:38][CH2:39][CH2:40][C:41]2[CH:42]=[CH:43][C:44]([OH:47])=[CH:45][CH:46]=2)=[CH:21][C:20]([O:23][C:24](=[O:28])[NH:25][CH2:26][CH3:27])=[CH:19][CH:18]=3)[CH:30]=[C:31]([CH3:36])[CH:32]=1

Participants

8

Reactant 3

HCID 176Acetic AcidHCID 86752673HCID 86752673, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 44365793HCID 44365793, compound

Reagents, catalysts & solvents 4

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethylcarbamic acid 3-(2-[benzyloxycarbonyl-[4-(4-benzyloxyphenyl)butyl]amino]-ethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl ester (12 mg in a mixture of 1.5 mL tetrahydrofuran and 0.5 mL methanol) was added 12 mg of 10% palladium hydroxide 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, 90:7:1) gave the title compound (8.2 mg). m/e=500 (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, 90:7:1)

Sources & evidence

ORD record
ord-ca669d22591c4466861e5aeae715b2d9
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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