Sodium hydride → HCID 67139799, compound

HRID 1592032Notes

Reaction equation

HRID 1592032 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:19])[CH:6]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:7]([O:9][CH3:10])=[O:8].[CH2:20]([O:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[N+:36]([O-:38])=[O:37])[CH2:31]I)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CCCCCC.CN(C=O)C.O>[CH3:3][O:4][C:5](=[O:19])[C:6]([CH2:31][C:30]1[CH:33]=[CH:34][C:35]([N+:36]([O-:38])=[O:37])=[C:28]([O:27][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:29]=1)([NH:11][C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[C:7]([O:9][CH3:10])=[O:8]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 4137603Dimethyl (Boc-amino)malonateHCID 67138462HCID 67138462, compound

Product 1

HCID 67139799HCID 67139799, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×HCID 8058HexaneSolvent

Procedure

Sodium hydride (60% in mineral oil, 729 mg, 18.22 mmol) is washed twice with dry hexane and suspended in DMF (15 mL). To the suspension is added dropwise a solution of t-butoxycarbonylamino-malonic acid dimethyl ester (4.92 g, 19.9 mmol) in DMF (15 mL) over a period of 10 min. The mixture is stirred at RT for 40 min and a solution of the title D compound, 3-benzyloxy-4-nitro-benzyl iodide (6.23 g, 16.9 mmol) in DMF (15 mL) is added dropwise over a period of 10 min and the mixture is stirred at RT overnight. The mixture is diluted with water (200 mL) and extracted 3 times with EtOAc. The organic extracts are washed with water and brine, dried over anhydrous MgSO4, filtered and evaporated. The residue is crystallized from ether-hexane to give 2-(3-benzyloxy-4-nitro-benzyl)-2-t-butoxycarbonylamino-malonic acid dimethyl ester: mp=114-116° C.

Workup

  1. stirringthe mixture is stirred at RT overnight
  2. extractionextracted 3 times with EtOAc
  3. washThe organic extracts are washed with water and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is crystallized from ether-hexane

Sources & evidence

ORD record
ord-b92e84d1be7c42c0afdc5dddfd39a18d
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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