Triethylamine → HCID 86756752, compound

HRID 1978086Notes

Reaction equation

HRID 1978086 reaction equation
C([O:5][C:6]([C@H:8]([C@@H:14]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:15]([NH:17][N:18]([CH2:23][CH:24]([CH3:26])[CH3:25])[S:19]([CH3:22])(=[O:21])=[O:20])=[O:16])[CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])=[O:7])(C)(C)C.C(N(CC)CC)C.O([Si](C)(C)C)S(C(F)(F)F)(=O)=O>O1CCOCC1>[C:6]([C@H:8]([C@@H:14]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:15]([NH:17][N:18]([CH2:23][CH:24]([CH3:25])[CH3:26])[S:19]([CH3:22])(=[O:21])=[O:20])=[O:16])[CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])([OH:7])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 86756753HCID 86756753, compound

Product 1

HCID 86756752HCID 86756752, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1.5 g of 2(R)-[1(S)-(tertbutoxycarbonyl)-4-methyl-3-pentenyl]-2′-isobutyl-2′-(methanesulphonyl)-4-methylvalerohydrazide, 0.51 g of triethylamine and 0.93 g trimethylsilyl triflate in 20 ml of 1,4-dioxane was heated at reflux under a nitrogen atmosphere for 4 hours. The mixture was cooled and the solvent was evaporated. The residue was dissolved in ethyl acetate and washed with 2M aqueous hydrochloric acid, water and brine. The ethyl acetate phase was then dried over anhydrous magnesium sulphate and the solvent was evaporated to give 1.31 g of 2(R)-[1(S)-(carboxy)-4-methyl-3-pentenyl]-2′-isobutyl-2′-(methanesulphonyl)-4-methylvalerohydrazide in the form of a yellow foam.

Workup

  1. temperatureat reflux under a nitrogen atmosphere for 4 hours
  2. temperatureThe mixture was cooled
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 2M aqueous hydrochloric acid, water and brine
  6. dry with materialThe ethyl acetate phase was then dried over anhydrous magnesium sulphate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-73eb57dd8b2d4657b70ac4dabc2d0795
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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