Valeryl chloride → Benzyl-{2-[2-(3,5-dimethylphenyl)-5-pentanoylamino-1H-indol-3-yl]ethyl}carbamic acid tert-butyl ester

HRID 1532379Notes

Reaction equation

HRID 1532379 reaction equation
[C:1]([O:5][C:6](=[O:35])[N:7]([CH2:15][CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([NH2:26])[CH:24]=2)[NH:19][C:18]=1[C:27]1[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[CH:28]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:36](Cl)(=[O:41])[CH2:37][CH2:38][CH2:39][CH3:40]>C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:35])[N:7]([CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:15][CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([NH:26][C:36](=[O:41])[CH2:37][CH2:38][CH2:39][CH3:40])[CH:24]=2)[NH:19][C:18]=1[C:27]1[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[CH:28]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 61186Valeryl chlorideHCID 53723321{2-[5-amino-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}benzylcarbamic acid tert-butyl ester

Product 1

HCID 54425158Benzyl-{2-[2-(3,5-dimethylphenyl)-5-pentanoylamino-1H-indol-3-yl]ethyl}carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of {2-[5-amino-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}benzylcarbamic acid tert-butyl ester (200 mg in 10 mL dry methylene chloride) at 0° C. was added 0.18 mL triethylamine followed by the dropwise addition of 0.06 mL valeryl chloride and the mixture stirred at low temperature. After 17 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 saturated sodium bicarbonate and saturated ammonium chloride then dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (hexane:ethyl acetate, 3:2) gave the title compound (230 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 saturated sodium bicarbonate and saturated ammonium chloride
  4. dry with materialthen dried over sodium sulfate
  5. customPurification of the
  6. concentrationconcentrate by flash chromatography on silica gel (hexane:ethyl acetate, 3:2)

Sources & evidence

ORD record
ord-cde92c1317444ef1855cadc4ec0a651c
Source dataset
uspto-grants-2001_03
Patent number
US06200957B1

Reaction notes

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