Trimethylsilyl triflate → 4-Methylpentanehydrazide

HRID 1978080Notes

Reaction equation

HRID 1978080 reaction equation
O1CCC(=CC[C@H](C(OC(C)(C)C)=O)[C@@H:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11](O)=[O:12])CC1.C([NH:29][NH2:30])C(C)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O>O1CCOCC1>[CH3:16][CH:15]([CH3:17])[CH2:14][CH2:10][C:11]([NH:29][NH2:30])=[O:12]

Participants

5

Reactant 3

HCID 65367Trimethylsilyl triflateHCID 542420IsobutylhydrazineHCID 69943268HCID 69943268, compound

Product 1

HCID 229948234-Methylpentanehydrazide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a manner analogous to that described in Example 2, parts (iii)-(v), starting from 4-tert-butyl hydrogen 3(S)-[(tetrahydro-2H-pyran-4-ylidene)ethyl]-2(R)-isobutylsuccinate and isobutylhydrazine and using trimethylsilyl trifluoromethanesulphonate in 1,4-dioxane instead of trifluoroacetic acid to deprotect the tertiary butyl ester there was obtained 2(R)-[3-(tetrahydro-2H-pyran-4-ylidene)-1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-propyl]-2′-isobutyl-2′-methanesulphonyl)-4-methylvalerohydrazide in the form of an off-white solid.

Sources & evidence

ORD record
ord-bc181703633e443da40f8a908dec524a
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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