Triethylamine → N-p-methoxybenzyl-N-tert.-butylthiomethyl-2-(S)-bromo-3-(R)-hydroxybutyramide

HRID 542364Notes

Reaction equation

HRID 542364 reaction equation
[Br:1][C@@H:2]([C@H:6]([OH:8])[CH3:7])[C:3]([OH:5])=O.[Cl-].[CH3:10][O:11][C:12]1[CH:25]=[CH:24][C:15]([CH2:16][NH2+:17][CH2:18][S:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:14][CH:13]=1.C1(N=C=NC2CCCCC2)CCCCC1.C(N(CC)CC)C>>[CH3:10][O:11][C:12]1[CH:25]=[CH:24][C:15]([CH2:16][N:17]([CH2:18][S:19][C:20]([CH3:21])([CH3:23])[CH3:22])[C:3](=[O:5])[C@@H:2]([Br:1])[C@H:6]([OH:8])[CH3:7])=[CH:14][CH:13]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 10921164(2S,3R)-2-bromo-3-hydroxybutanoic acidHCID 86741051N-p-methoxybenzyl-N-tert-butylthiomethylammonium chloride

Product 1

HCID 13923694N-p-methoxybenzyl-N-tert.-butylthiomethyl-2-(S)-bromo-3-(R)-hydroxybutyramide

Procedure

To a solution of 1.83 g (10 mmol) of (2S,3R)-2-bromo-3-hydroxybutyric acid, manufactured analogously to a method prescribed by Shimohigashi et al., Bull. Chem. Soc. Japan 52, 949 (1979), there are added in succession, at room temperature, 2.76 g (10 mmol) of N-p-methoxybenzyl-N-tert.-butylthiomethylammonium chloride, 2.06 g (10 mmol) of dicyclohexyl carbodiimide and, dropwise, 1.40 ml (10 mmol) of triethylamine. The resulting reaction mixture is stirred at room temperature for 2 hours. The dicyclohexylurea which has separated out is filtered off with suction, and the filtrate is diluted with methylene chloride and washed with water and phosphate buffer solution of pH 8. The organic phase is dried over sodium sulphate and concentrated by evaporation, and the oily residue is chromatographed over silica gel with toluene/ethyl acetate. The title compound is obtained in the form of a colourless, viscous oil. Rf (toluene/ethyl acetate 1:1): 0.55; IR (in methylene chloride): 3550-3200, 2950-2850, 1632, 1608, 1508, 1457, 1438, 1407, 1360, 1242, 1202, 1175, 1150, 1028 cm-1.

Workup

  1. additionJapan 52, 949 (1979), there are added in succession, at room temperature
  2. customThe resulting reaction mixture
  3. customThe dicyclohexylurea which has separated out
  4. filtrationis filtered off with suction
  5. additionthe filtrate is diluted with methylene chloride
  6. washwashed with water and phosphate buffer solution of pH 8
  7. dry with materialThe organic phase is dried over sodium sulphate
  8. concentrationconcentrated by evaporation
  9. customthe oily residue is chromatographed over silica gel with toluene/ethyl acetate

Sources & evidence

ORD record
ord-36503b85247449e397f609f6685958d8
Source dataset
uspto-grants-1987_04
Patent number
US04656165

Reaction notes

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