Dichloromethane → HCID 13923698, compound

HRID 542365Notes

Reaction equation

HRID 542365 reaction equation
N12CCCCC1C=NCCC2.[CH3:12][O:13][C:14]1[CH:36]=[CH:35][C:17]([CH2:18][N:19]([CH2:27][S:28]([C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:30])=[O:29])[C:20](=[O:26])[C@@H:21](Br)[C@H:22]([OH:24])[CH3:23])=[CH:16][CH:15]=1.C(Cl)Cl>O1CCCC1>[CH3:12][O:13][C:14]1[CH:36]=[CH:35][C:17]([CH2:18][N:19]([CH2:27][S:28]([C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:30])=[O:29])[C:20](=[O:26])[C@@H:21]2[O:24][C@@H:22]2[CH3:23])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 13923696HCID 13923696, compound

Product 1

HCID 13923698HCID 13923698, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At -14° with the exclusion of moisture, 340 ml of 1,5-diazabicyclo[5.4.0]undec-5-ene in 1 ml of tetrahydrofuran are added to a solution of 486 mg (1.1 mmol) of (2S,3R)-N-p-methoxybenzyl-N-tert.-butylsulphonylmethyl-2-bromo-3-hydroxybutyramide in 8 ml of tetrahydrofuran. The solution is stirred at room temperature for 75 minutes. After the addition of methylene chloride, the organic phase is extracted by shaking with 15% aqueous citric acid solution and 8% aqueous sodium bicarbonate solution. The organic phase is dried over sodium sulphate and concentrated by evaporation under reduced pressure. After chromatography of the residue over silica gel with toluene/ethyl acetate (4:1), the title compound is obtained in the form of a colourless, viscous oil. Rf (toluene/ethyl acetate 1:1): 0.29; [α]=+45± 1° (1.065% in CHCl3). The 1H-NMR spectrum (400 MHz in CDCl3) points to the existence of two rotamers in a ratio of 1:2.8.

Workup

  1. extractionthe organic phase is extracted
  2. stirringby shaking with 15% aqueous citric acid solution and 8% aqueous sodium bicarbonate solution
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-7bc20bac94a846b694bc06f35ab4dfab
Source dataset
uspto-grants-1987_04
Patent number
US04656165

Reaction notes

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