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

HRID 542364노트

반응식

HRID 542364 반응식
[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

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-36503b85247449e397f609f6685958d8
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04656165

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