N-methoxy-N-methylpentanamide → HCID 18946711, compound

HRID 248926Notes

Reaction equation

HRID 248926 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])(CC)C.CON(C)[C:24](=[O:29])[CH2:25][CH2:26][CH2:27][CH3:28]>O1CCCC1.CCOCC>[C:1]([O:5][C:6]([NH:8][C:9]1[C:14]([CH2:15][C:24](=[O:29])[CH2:25][CH2:26][CH2:27][CH3:28])=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 3801384N-methoxy-N-methylpentanamideHCID 117458482-(N-Boc-Amino)-3-methylpyridineHCID 178418400CID 53628100

Product 1

HCID 18946711HCID 18946711, compoundYield 57.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(t-butoxycarbonylamino)-3-methylpyridine (X) (5.3 g) (prepared, e.g., as described in Preparation 17), in tetrahydrofuran (100 ml) was cooled to -50° C. and a solution of sec-butyllithium (46 ml of 1.3M in cyclohexane) was added. After 10 minutes, the dark solution was treated with N-methoxy-N-methylvaleramide (4.4 g) and the resulting solution was stirred 10 minutes. The mixture was diluted with ether, washed with water, dried over sodium sulfate and evaporated. Crystallization of the residue from hexane afforded 1-[2-(t-butoxycarbonylamino)pyridin-3-yl]hexan-2-one (4.3 g), a compound of Formula (Y), as a white solid m.p. 66°-67° C.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customCrystallization of the residue from hexane

Sources & evidence

ORD record
ord-f12d923fa9d04029b644e8a83c02a736
Source dataset
uspto-grants-1993_05
Patent number
US05212195

Reaction notes

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