Water → HCID 66616121, compound

HRID 2367066Notes

Reaction equation

HRID 2367066 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH3:22])([CH3:21])[C:13]2=[O:23])[CH2:8][CH2:7]1)=[O:5].C(N(CC)CC)C.[N+:39]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[S:48](Cl)(=[O:50])=[O:49])([O-:41])=[O:40].O>ClCCl.C(OCC)(=O)C>[CH3:21][C:14]1([CH3:22])[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:12]([CH:9]2[CH2:8][CH2:7][N:6]([C:4](=[O:5])[C@@H:3]([NH:2][S:48]([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=3[N+:39]([O-:41])=[O:40])(=[O:49])=[O:50])[CH2:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:11][CH2:10]2)[C:13]1=[O:23]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 66616074HCID 66616074, compound

Product 1

HCID 66616121HCID 66616121, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-1-(1-(2-amino-4-phenylbutanoyl)piperidin-4-yl)-3,3-dimethylindolin-2-one hydrochloride (1.00 g, 2.26 mmol, EXAMPLE 1, Step 4) in dichloromethane (10 mL) was added triethylamine (954 microL, 6.79 mmol) and 2-nitrobenzenesulfonyl chloride (501 mg, 2.26 mmol) at 0° C. After stirring for 20 min at room temperature, water and ethyl acetate were added to the mixture. The organic layer was washed with sodium hydrogen carbonate aqueous solution, 1 mol/L hydrochloric acid and brine, dried over sodium sulfate and concentrated. The crude product was purified by silica gel column chromatography (hexane/ethyl acetate, gradient) to give the title compound (1.26 g, 94%) as an amorphous solid.

Workup

  1. washThe organic layer was washed with sodium hydrogen carbonate aqueous solution, 1 mol/L hydrochloric acid and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel column chromatography (hexane/ethyl acetate, gradient)

Sources & evidence

ORD record
ord-35133e75aeb346e080ac33e2708f5732
Source dataset
uspto-grants-2014_04
Patent number
US08697877B2

Reaction notes

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