Ethanol → HCID 21254089, compound

HRID 1531562Notes

Reaction equation

HRID 1531562 reaction equation
C(OC(=O)[N:10]([CH2:26][CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([C:37]([CH3:46])([CH3:45])[C:38](=[O:44])[N:39]3[CH2:43][CH2:42][CH2:41][CH2:40]3)[CH:35]=2)[NH:30][C:29]=1[C:47]1[CH:52]=[C:51]([CH3:53])[CH:50]=[C:49]([CH3:54])[CH:48]=1)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][CH:16]=1)C1C=CC=CC=1.C(O)C.[H][H].[NH4+].[OH-]>[OH-].[OH-].[Pd+2].C(O)(=O)C.C(OCC)(=O)C>[CH3:46][C:37]([C:34]1[CH:35]=[C:36]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29]([C:47]1[CH:52]=[C:51]([CH3:53])[CH:50]=[C:49]([CH3:54])[CH:48]=1)=[C:28]2[CH2:27][CH2:26][NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][S:22]([CH3:25])(=[O:23])=[O:24])=[CH:19][CH:20]=1)([CH3:45])[C:38](=[O:44])[N:39]1[CH2:43][CH2:42][CH2:41][CH2:40]1

Participants

8

Reactant 4

HCID 702EthanolHCID 14923Ammonium HydroxideHCID 70223390HCID 70223390, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21254089HCID 21254089, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 52.6 mg (0.069 mmol) of [2-[5-(1,1-dimethyl-2-oxo-2-pyrrolidin-1-ylethyl)-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl]-[4-(4-methanesulfonylaminophenyl)butyl]carbamic acid benzyl ester (from Step 1), 25 mg of 20% palladium hydroxide on carbon, 2.5 mL of ethanol, 2.5 mL of ethyl acetate, and 0.010 mL of glacial acetic acid was shaken with hydrogen (approx. 45 psig) in a pressure vessel for 1.8 hours. The catalyst was removed by filtration through Celite, and the filtrate was concentrated in vacuo. The residue was purified by preparative TLC on 4 Analtech tapered silica gel GF plates (developed in 92.5:7.5:0.75 CH2Cl2-MeOH-concd. NH4OH; product band extracted with the same solvent) yielded 38.4 mg (88%) of cream-colored, stiff foam; homogeneous by TLC in in 92.5:7.5:0.75 CH2Cl2-MeOH-concd. NH4OH. 500 MHz 1H NMR (CDCl3) was consistent with the assigned structure. Mass spectrum (ESI): m/e 629.6 (M+H)+.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by preparative TLC on 4 Analtech
  4. extractionproduct band extracted with the same solvent)
  5. customyielded 38.4 mg (88%) of cream-colored, stiff foam

Sources & evidence

ORD record
ord-81c9b2822529459487c952ad077271c7
Source dataset
uspto-grants-2001_03
Patent number
US06197975B1

Reaction notes

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