(+)-Benzyl 3-{1-(1,3-benzodioxol-5-yl)-2-[(2-methoxy-4-methylphenyl)sulfonylamino]-2-oxoethyl}-1-methyl-1H-indole-6-carboxylate → (s)-(+)-3-{1-(1,3-Benzodioxol-5-yl)-2-[(2-methoxy4-methylphenyl)-sulfonylamino]-2-oxoethyl}-1-methyl-1h-indole-6-carboxylic acid

HRID 322088Notes

Reaction equation

HRID 322088 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:26]3[C:34]4[C:29](=[CH:30][C:31]([C:35]([O:37]CC5C=CC=CC=5)=[O:36])=[CH:32][CH:33]=4)[N:28]([CH3:45])[CH:27]=3)[C:11]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=3[O:24][CH3:25])(=[O:16])=[O:15])=[O:12])=[CH:9][C:4]=2[O:3][CH2:2]1.[H][H]>C(O)C.[Pd]>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@@H:10]([C:26]3[C:34]4[C:29](=[CH:30][C:31]([C:35]([OH:37])=[O:36])=[CH:32][CH:33]=4)[N:28]([CH3:45])[CH:27]=3)[C:11]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=3[O:24][CH3:25])(=[O:15])=[O:16])=[O:12])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 2

HCID 20642448(+)-Benzyl 3-{1-(1,3-benzodioxol-5-yl)-2-[(2-methoxy-4-methylphenyl)sulfonylamino]-2-oxoethyl}-1-methyl-1H-indole-6-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 9807200(s)-(+)-3-{1-(1,3-Benzodioxol-5-yl)-2-[(2-methoxy4-methylphenyl)-sulfonylamino]-2-oxoethyl}-1-methyl-1h-indole-6-carboxylic acidYield 90.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(+)-Benzyl 3-{1-(1,3-benzodioxol-5-yl)-2-[(2-methoxy-4-methylphenyl)sulfonylamino]-2-oxoethyl}-1-methyl-1H-indole-6-carboxylate (from (f), 374 mg) was dissolved in aqueous ethanol (20 ml of 9:1 ethanol/water) and 50 mg of 5% palladium on carbon was added. After 3 h at 414 kPa (60 psi) of hydrogen at room temperature a further 50 mg of catalyst was added and the hydrogenation continued for a further 3 h. The catalyst was removed by filtration and the filtrate evaporated. The residue was azeotroped several times with dichloromethane to give the title compound (290 mg) in >98%ee (determined by chiral HPLC).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated
  3. customThe residue was azeotroped several times with dichloromethane

Sources & evidence

ORD record
ord-312d3259164d4ed48f98af1cdaf6f658
Source dataset
uspto-grants-2001_04
Patent number
US06211223B1

Reaction notes

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