Acetic Acid → HCID 44365771, compound

HRID 1531544Notes

Reaction equation

HRID 1531544 reaction equation
C(OC([N:11]([CH2:40][CH2:41][CH2:42][CH2:43][C:44]1[CH:49]=[CH:48][C:47]([O:50]CC2C=CC=CC=2)=[CH:46][CH:45]=1)[CH2:12][CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][C:24]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:25])[CH:21]=2)[NH:16][C:15]=1[C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=1)=O)C1C=CC=CC=1.C(O)(=O)C.[H][H]>O1CCCC1.CO.[Pd].O>[CH3:39][C:34]1[CH:33]=[C:32]([C:15]2[NH:16][C:17]3[C:22]([C:14]=2[CH2:13][CH2:12][NH:11][CH2:40][CH2:41][CH2:42][CH2:43][C:44]2[CH:49]=[CH:48][C:47]([OH:50])=[CH:46][CH:45]=2)=[CH:21][C:20]([O:23][C:24]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[O:25])=[CH:19][CH:18]=3)[CH:37]=[C:36]([CH3:38])[CH:35]=1

Participants

8

Reactant 3

HCID 176Acetic AcidHCID 54123530HCID 54123530, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 44365771HCID 44365771, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of morpholine-4-carboxylic acid 3-(2-[benzyloxycarbonyl-[4-(4-benzyloxy-phenyl)butyl]amino]-ethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl ester (20 mg in a mixture of 2 mL tetrahydrofuran and 0.5 mL methanol) was added 16.8 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, 90:7:1) gave the title compound (12 mg). m/e=542 (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-b9fa9608e0e84af9a1e68b7e2aa27e90
Source dataset
uspto-grants-2001_03
Patent number
US06197975B1

Reaction notes

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