Triethylamine → D-Serine N-(2-methylthio-2,4-dimethylpentan-3-yl)amide

HRID 462851Notes

Reaction equation

HRID 462851 reaction equation
C(OC([NH:8][C@@H:9]([C:12]([OH:14])=O)[CH2:10][OH:11])=O)(C)(C)C.C(N(CC)CC)C.ClC(OCC)=O.[CH3:28][S:29][C:30]([CH3:37])([CH:32]([NH2:36])[CH:33]([CH3:35])[CH3:34])[CH3:31]>C(OCC)(=O)C.O1CCCC1>[CH3:28][S:29][C:30]([CH3:37])([CH:32]([NH:36][C:12](=[O:14])[C@@H:9]([CH2:10][OH:11])[NH2:8])[CH:33]([CH3:35])[CH3:34])[CH3:31]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 637603(R)-2-tert-butoxycarbonylamino-3-hydroxy propionic acidHCID 144058322-Methylthio-2,4-dimethyl-3-aminopentane

Product 1

HCID 54125361D-Serine N-(2-methylthio-2,4-dimethylpentan-3-yl)amide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3.47 g. (0.017 mole) of N-t-butoxycarbonyl-D-serine and 2.5 g. (0.017 mole) triethylamine in 100 ml. of tetrahydrofuran at -15° C. is added 1.63 ml. of ethyl chloroformate. After stirring for 15 minutes, 2.49 g. (0.017 mole) 2-methylthio-2,4-dimethyl-3-aminopentane is added and the mixture stirred for one hour. The reaction mixture is diluted with ethyl acetate, washed with water, 5% aqueous citric acid (w/v), sodium bicarbonate solution and brine. The organic phase is evaporated to dryness. The residue is taken up in 100 ml. methanol, 60 ml. of concentrated hydrochloric acid added and the mixture refluxed for one hour. After evaporation of methanol, the residue is taken up in water, washed with ether, the aqueous phase adjusted to pH 12 with sodium hydroxide and extracted with ethyl ether. Evaporation of the extracts affords the desired D-serine amide.

Workup

  1. stirringthe mixture stirred for one hour
  2. washwashed with water, 5% aqueous citric acid (w/v), sodium bicarbonate solution and brine
  3. customThe organic phase is evaporated to dryness
  4. additionof concentrated hydrochloric acid added
  5. temperaturethe mixture refluxed for one hour
  6. customAfter evaporation of methanol
  7. washwashed with ether
  8. extractionextracted with ethyl ether
  9. customEvaporation of the extracts

Sources & evidence

ORD record
ord-45d55eae472a4bf884d316f8f7b43c29
Source dataset
uspto-grants-1985_05
Patent number
US04517379

Reaction notes

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