Diethyl 2-((tert-butoxycarbonyl)amino)malonate → Diethyl 2-(2-benzyloxy-5-iodobenzyl)-2-tert-butoxycarbonylaminomalonate

HRID 269596

Reaction equation

HRID 269596 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=1[CH2:16]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([O:22][C:23]([NH:25][CH:26]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:24])([CH3:21])([CH3:20])[CH3:19].[O-]CC.[Na+]>C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=1[CH2:16][C:26]([NH:25][C:23]([O:22][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:24])([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 382219Diethyl 2-((tert-butoxycarbonyl)amino)malonateHCID 2723922Sodium ethoxideHCID 114182311-Benzyloxy-2-bromomethyl-4-iodobenzene

Product 1

HCID 66879924Diethyl 2-(2-benzyloxy-5-iodobenzyl)-2-tert-butoxycarbonylaminomalonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

41 g (101.7 mmol) of 1-benzyloxy-2-bromomethyl-4-iodobenzene (Example 4A) are added to a solution of 28 g (101.7 mmol) of diethyl 2-[N-(tert-butoxycarbonyl)amino]malonate and 7.9 ml (101.7 mmol) of sodium ethoxide in 300 ml of ethanol. After stirring at RT for 3 h, the precipitated product is collected by suction filtration. After drying in vacuo, 55 g (90% of theory) of product are isolated.

Workup

  1. filtrationthe precipitated product is collected by suction filtration
  2. customAfter drying in vacuo, 55 g (90% of theory) of product
  3. customare isolated

Sources & evidence

ORD record
ord-8c030366cae84f828a34666b360855c4
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Linked notes

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