HCID 67664460, compound → HCID 67636969, compound

HRID 1458377Notes

Reaction equation

HRID 1458377 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17](=[O:22])NCOC)=[CH:14][CH:15]=2)[C:10]([CH2:23][CH2:24][N:25]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:26][CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)=[C:9]1[C:43]1[CH:48]=[C:47]([CH3:49])[CH:46]=[C:45]([CH3:50])[CH:44]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:51][Li]>CCOCC>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17](=[O:22])[CH3:51])=[CH:14][CH:15]=2)[C:10]([CH2:23][CH2:24][N:25]([C:36]([O:38][C:39]([CH3:41])([CH3:40])[CH3:42])=[O:37])[CH2:26][CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)=[C:9]1[C:43]1[CH:44]=[C:45]([CH3:50])[CH:46]=[C:47]([CH3:49])[CH:48]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 67664460HCID 67664460, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 67636969HCID 67636969, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-{2-[tert-butoxycarbonyl-(4-pyridin-4-yl-butyl)amino]ethyl}-2-(3,5 -dimethylphenyl)-5-(methoxymethylcarbamoyl) indole-1-carboxylic acid tert-butyl ester (0.069 g in 3 mL dry tetrahydrofuran) at -10° C. was added 0.20 mL of a 1.5M solution of methyllithium in ether and the mixture stirred at low temperature. After 45 minutes, the reaction was quenched by the addition of saturated aqueous ammonium chloride and extracted with ethyl acatate. The organic portion was washed with brine, dried over sodium sulfate and the concentrate purified by preparative TLC on silica gel (hexane:ethyl acetate, 2:3) to give the title compound (58 mg).

Workup

  1. customthe reaction was quenched by the addition of saturated aqueous ammonium chloride
  2. extractionextracted with ethyl acatate
  3. washThe organic portion was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe concentrate purified by preparative TLC on silica gel (hexane:ethyl acetate, 2:3)

Sources & evidence

ORD record
ord-489fc6d4c8424ee1b5e0680a951ce721
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

Loading…