Lithium Hydroxide → HCID 68717561, compound

HRID 1444562Notes

Reaction equation

HRID 1444562 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH:5]([NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].I[CH2:24][CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27].[OH-].[Li+]>CN1CCCC1=O>[CH2:9]([O:8][C:6](=[O:7])[C:5]([NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])([CH2:24][CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[C:4]([O:3][CH2:1][CH3:2])=[O:22])[CH3:10]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 259787Diethyl 2-(benzyloxycarbonylamino)malonateHCID 1145850824346-54-1

Product 1

HCID 68717561HCID 68717561, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 2-benzyloxycarbonylaminomalonic acid diethyl ester (Bladon, C. M. J. Chem. Soc. Perkin Trans. 1990, 1, 1151-1158) (1.237 g), iodo-2-ethylbutane (1.272 g) and lithium hydroxide (0.287 g) in N-methylpyrrolidone (8 mL) was stirred for 2 days at room temperature and then diluted with ice water. The aqueous solution was extracted with ether and the product purified by chromatography on silica gel to give 2-benzyloxycarbonylamino-2-(2-ethylbutyl)malonic acid diethyl ester (0.520 g).

Workup

  1. extractionThe aqueous solution was extracted with ether
  2. customthe product purified by chromatography on silica gel

Sources & evidence

ORD record
ord-4c55920be2a24f56bd2e9cce8bf45af4
Source dataset
uspto-grants-2010_02
Patent number
US07662849B2

Reaction notes

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