Methyl iodide → HCID 68500872, compound

HRID 1176639Notes

Reaction equation

HRID 1176639 reaction equation
C(O[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:21]2[CH:22]=[C:23]([CH2:26][O:27][CH:28]3[CH:33]([C:34]4[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][CH2:43][O:44][CH2:45][C:46]5[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=5[O:52][CH3:53])=[CH:36][CH:35]=4)[CH2:32][CH2:31][N:30]([C:54]([O:56][CH2:57][C:58]4[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=4)=[O:55])[CH2:29]3)[CH:24]=[CH:25][C:20]=2[O:19][CH2:18][C:17]1=[O:64])=O)C1C=CC=CC=1.[H-].[Na+].CI.[C:69](=[O:72])([O-:71])O.[Na+]>CN(C)C=O>[CH2:26]([O:71][C:69]([CH2:9][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:21]2[CH:22]=[C:23]([CH2:26][O:27][CH:28]3[CH:33]([C:34]4[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][CH2:43][O:44][CH2:45][C:46]5[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=5[O:52][CH3:53])=[CH:36][CH:35]=4)[CH2:32][CH2:31][N:30]([C:54]([O:56][CH2:57][C:58]4[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=4)=[O:55])[CH2:29]3)[CH:24]=[CH:25][C:20]=2[O:19][CH2:18][C:17]1=[O:64])=[O:72])[C:23]1[CH:24]=[CH:25][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 68503536HCID 68503536, compound

Product 1

HCID 68500872HCID 68500872, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The stirred solution of 0.351 g of benzyl 3-[4-(4-benzyloxycarbonylaminobutyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate and 8 ml of N,N-dimethylformamide is admixed at 0° C. with 0.031 g of sodium hydride (60% dispersion). After 1 hour, 0.144 ml of methyl iodide is added and the mixture is kept at 75° C. over 18 hours. The mixture is cooled, poured onto aqueous 1M sodium hydrogencarbonate solution (40 ml) and extracted with ethyl acetate (2×40 ml). The organic phases are washed with brine (40 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.17 (1:1 EtOAc-heptane); Rt=6.18.

Workup

  1. waitthe mixture is kept at 75° C. over 18 hours
  2. temperatureThe mixture is cooled
  3. extractionextracted with ethyl acetate (2×40 ml)
  4. washThe organic phases are washed with brine (40 ml)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-c7d2858f3c9847a298cf4901194fbf88
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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