5-Aminovaleric acid → 6-(Tert-butoxy)-6-oxohexanoic acid

HRID 722705Notes

Reaction equation

HRID 722705 reaction equation
N[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].C(N(CC)CC)C.[CH3:16][C:17]([O:20][C:21](ON=C(C1C=CC=CC=1)C#N)=[O:22])([CH3:19])[CH3:18]>O1CCOCC1>[C:17]([O:20][C:21]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7])=[O:22])([CH3:19])([CH3:18])[CH3:16]

Participants

5

Reactant 3

HCID 1385-Aminovaleric acidHCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Product 1

HCID 159089376-(Tert-butoxy)-6-oxohexanoic acidYield 52.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Prepared as described for L3 from stirring 5-aminopentanoic acid (3.40 g, 29.1 mmol) in 50% aqueous dioxane with triethylamine (6.0 mL, 43.1 mmol) and BOC-ON (7.91 g, 32.1 mmol) to yield a cream solid (3.10 g, 48.8%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0823345e1dc540b29bdcfc05b5e54da5
Source dataset
uspto-grants-2006_11
Patent number
US07138520B2

Reaction notes

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