Dimethyl Sulfoxide → N-benzyl-O-methyl-N2-trityl-D-serinamide

HRID 420114Notes

Reaction equation

HRID 420114 reaction equation
CS(C)=O.[OH-].[K+].[CH2:7]([NH:14][C:15](=[O:39])[C@@H:16]([CH2:37][OH:38])[NH:17][C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:40]I>C1(C)C=CC=CC=1.O>[CH2:7]([NH:14][C:15](=[O:39])[C@@H:16]([CH2:37][O:38][CH3:40])[NH:17][C:18]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 57734155N-benzyl-N2-trityl-D-serinamide

Product 1

HCID 54752467N-benzyl-O-methyl-N2-trityl-D-serinamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a mixture of DMSO (8 g) and pulverized KOH (0.308 g), Example 5 product (i.e., N-benzyl-N2-trityl-D-serinamide, 2 g) was added in one lot. It was stirred for 3 hours at ambient temperature. Methyl iodide (0.97 g) was slowly added to the mixture for 15 minutes at ambient temperature and stirred for 30 minutes. The reaction mixture was cooled to 0° C., water was added to it and the product was isolated with toluene. Oily product was recovered under vacuum at 35-40° C. from the organic layer. Hexane (100 ml) was added to the oily product and the solution formed is stirred for 15 minutes, filtered and dried to get the titled product of Formula Va. Yield=1 gm.

Workup

  1. additionwas added in one lot
  2. stirringstirred for 30 minutes
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. customOily product was recovered under vacuum at 35-40° C. from the organic layer
  5. additionHexane (100 ml) was added to the oily product
  6. customthe solution formed
  7. stirringis stirred for 15 minutes
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-82e7999818474ac89839e691d16171e0
Source dataset
uspto-grants-2012_01
Patent number
US08093426B2

Reaction notes

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