Acetic Anhydride → HCID 70223405, compound

HRID 1531571Notes

Reaction equation

HRID 1531571 reaction equation
[C:1]([O:5][C:6](=[O:47])[N:7]([CH2:27][CH2:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([NH2:38])[CH:36]=2)[NH:31][C:30]=1[C:39]1[CH:44]=[C:43]([CH3:45])[CH:42]=[C:41]([CH3:46])[CH:40]=1)[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([S:19]([CH3:22])(=[O:21])=[O:20])[C:13]=1[S:23]([CH3:26])(=[O:25])=[O:24])([CH3:4])([CH3:3])[CH3:2].[C:48](OC(=O)C)(=[O:50])[CH3:49]>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:47])[N:7]([CH2:27][CH2:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([NH:38][C:48](=[O:50])[CH3:49])[CH:36]=2)[NH:31][C:30]=1[C:39]1[CH:40]=[C:41]([CH3:46])[CH:42]=[C:43]([CH3:45])[CH:44]=1)[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([S:19]([CH3:22])(=[O:20])=[O:21])[C:13]=1[S:23]([CH3:26])(=[O:25])=[O:24])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 70226124HCID 70226124, compound

Product 1

HCID 70223405HCID 70223405, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of {2-[5-amino-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}-[4-(4-amino(dimethanesulfonyl)phenyl)butyl] carbamic acid tert-butyl ester (from EXAMPLE 3.2 StepC, 60 mg in 3 mL dry methylene chloride) at 0° C. was added 0.025 mL pyridine followed by 0.020 mL acetic anhydride and the mixture stirred at low temperature. After 15 minutes, the reaction was quenched by the addition of saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic portion was washed successively with a pH2 solution, saturated sodium bicarbonate and brine, then dried over sodium sulfate. Concentration in vacuo provided the crude title compound (65 mg).

Workup

  1. customthe reaction was quenched by the addition of saturated aqueous sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. washThe organic portion was washed successively with a pH2 solution, saturated sodium bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-c1cd02829af5424381432c89a6b22547
Source dataset
uspto-grants-2001_03
Patent number
US06197975B1

Reaction notes

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