tert-Butyl acetate → HCID 67083028, compound

HRID 2368682Notes

Reaction equation

HRID 2368682 reaction equation
[C:1]([C:6]1[C:7]([NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[N:8][CH:9]=[CH:10][CH:11]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].[Li+].CC([N-]C(C)C)C.[C:27]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:29])[CH3:28]>>[OH:5][C:1]([C:6]1[C:7]([NH:12][C:13](=[O:18])[C:14]([CH3:16])([CH3:15])[CH3:17])=[N:8][CH:9]=[CH:10][CH:11]=1)([CH:2]([CH3:4])[CH3:3])[CH2:28][C:27]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]

Participants

4

Reactant 3

HCID 10908tert-Butyl acetateHCID 2724682Lithium diisopropylamideHCID 67083010N-(3-isobutyrylpyridin-2-yl)pivalamide

Product 1

HCID 67083028HCID 67083028, compound

Procedure

A solution of N-(3-isobutyrylpyridin-2-yl)pivalamide (3.10 g, 12.5 mmol), LDA (1.5 M, 17.50 mL, 2.1 eq) and t-butyl acetate (3.5 mL, 2.1 eq) were reacted as outlined in Scheme 1 to give tert-butyl 3-hydroxy-4-methyl-3-(2-pivalamidopyridin-3-yl)pentanoate which was used in the next step without further purification.

Sources & evidence

ORD record
ord-b5715b69f4cf4d8ab51f377c33c38c71
Source dataset
uspto-grants-2014_04
Patent number
US08703797B2

Reaction notes

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