Methyl iodide → HCID 22941572, compound

HRID 343644Notes

Reaction equation

HRID 343644 reaction equation
CI.[C:3](=O)([O-])O.[Na+].[C:8]([O:12][C:13]([NH:15][C@@H:16]([CH2:33][S:34][C:35]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:17][NH:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]([O:31][CH3:32])=[O:30])=[O:14])([CH3:11])([CH3:10])[CH3:9]>CN(C)C=O>[C:8]([O:12][C:13]([NH:15][C@@H:16]([CH2:33][S:34][C:35]([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH2:17][N:18]([C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]([O:31][CH3:32])=[O:30])[CH3:3])=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 22941571HCID 22941571, compound

Product 1

HCID 22941572HCID 22941572, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

3.6 cm3 of methyl iodide and 7 g of solid sodium hydrogen carbonate are added, with stirring, to a solution of 1.5 g of methyl 5-(2(R)-tert-butoxycarbonylamino-3-(triphenylmethylthio)-propylamino)-1-naphthoate in 25 cm3 of dimethyl-formamide. The reaction mixture is stirred for 20 hours at a temperature in the region of 20° C. and then poured onto 200 cm3 of ice. The aqueous phase is extracted 3 times with 150 cm3 of ethyl acetate. The organic phases are combined, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure. The red oil obtained is purified by chromatography on silica [eluent: cyclohexane/ethyl acetate (90/10 by volume)]. 0.56 g of methyl 5-(2(R)-tert-butoxycarbonylamino-3-(triphenylmethylthio)propyl-N-methylamino)-1-naphthoate is obtained, the characteristics of which are the following:

Workup

  1. extractionThe aqueous phase is extracted 3 times with 150 cm3 of ethyl acetate
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe red oil obtained
  6. customis purified by chromatography on silica [eluent: cyclohexane/ethyl acetate (90/10 by volume)]

Sources & evidence

ORD record
ord-6e81c43ce24c4af8829ad47be1711d54
Source dataset
uspto-grants-1999_01
Patent number
US05861529

Reaction notes

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