1,2-Dichloroethane → HCID 86746090, compound

HRID 847325Notes

Reaction equation

HRID 847325 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C@H:11]([CH2:20][C@@H:21]([CH:28]([CH3:30])[CH3:29])C/C=C/C(O)=O)[O:10][C:9]1([CH3:32])[CH3:31])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:33](Cl)[CH2:34]Cl.[CH:37]1[CH:38]=[CH:39][C:40]2N(O)N=N[C:41]=2[CH:42]=1.C(N1CC[O:52]CC1)C.C1C=C[C:58]([CH2:61][CH2:62][NH2:63])=[CH:57]C=1.S([O-])(O)(=O)=O.[K+].S([O-])([O-])(=O)=O.[K+].[K+]>C(Cl)Cl>[CH:14]1([CH2:13][C@H:12]2[C@H:11]([CH2:20][C@@H:21]([CH:28]([CH3:30])[CH3:29])[CH2:57][CH:58]=[CH:61][C:62](=[O:52])[NH:63][CH2:33][CH2:34][C:41]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:42]=3)[O:10][C:9]([CH3:32])([CH3:31])[N:8]2[C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

9

Reactant 7

HCID 111,2-DichloroethaneHCID 1001PhenethylamineHCID 7525EthylmorpholineHCID 24507Potassium SulfateHCID 757711-HydroxybenzotriazoleHCID 516920Potassium bisulfateHCID 67915583HCID 67915583, compound

Product 1

HCID 86746090HCID 86746090, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 0.63 g (1.39 mmol) of (E,S)-5-[[(4S,5S)-3-(t-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyl-5-oxazolidinyl]methyl]-6-methyl-2-heptenoic acid, 0.32 g (1.7 mmol) of EDC, 0.28 g (2 mmol) of HOBT and 20 ml of methylene chloride is cooled to -10°, treated with 0.35 ml (2.7 mmol) of N-ethylmorpholine and 0.26 ml (2 mmol) of 2-phenethylamine in 10 ml of methylene chloride and stirred at -10° for 1.5 hours and at room temperature for 20 hours. Thereafter, the reaction mixture is poured into ice-water, adjusted to pH 3 with a pH 2 buffer of potassium hydrogen sulphate and potassium sulphate and extracted with methylene chloride. The methylene chloride extracts are washed with 2N sodium carbonate solution, dried over magnesium sulphate and evaporated under reduced pressure. Chromatography of the residue on 7.5 g of silica gel yields 0.66 g of t-butyl (4S,5S)-4-(cyclohexylmethyl)-5-[(S)-2-isopropyl-5-(phenethylcarbamoyl)-4-pentenyl]-2,2-dimethyl-3-oxazolidinecarboxylate as a colourless resin, MS: 539 (M-CH3)+.

Workup

  1. temperatureis cooled to -10°
  2. extractionextracted with methylene chloride
  3. washThe methylene chloride extracts are washed with 2N sodium carbonate solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8f93f5d08bdf484b893796ff4eb4e05f
Source dataset
uspto-grants-1992_08
Patent number
US05140011

Reaction notes

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