Sodium hydride → HCID 66750738, compound

HRID 643873Notes

Reaction equation

HRID 643873 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[C:17]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][C:15]2[C:10](=[CH:11][C:12]([Br:26])=[CH:13][CH:14]=2)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:31][C:32]([O:34][CH3:35])=[O:33]>CN(C=O)C>[CH3:35][O:34][C:32](=[O:33])[CH2:31][N:7]([C:8]1[C:17]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:16][C:15]2[C:10](=[CH:11][C:12]([Br:26])=[CH:13][CH:14]=2)[CH:9]=1)[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:27]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 66750919HCID 66750919, compound

Product 1

HCID 66750738HCID 66750738, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3-benzyloxy-7-bromonaphthalen-2-yl)-carbamic acid tert-butyl ester (38.65 g, 90.2 mmol) in DMF (300 mL) at 0° C. is added NaH (3.79 g, 99.3 mmol). To the solution is added methyl bromoacetate (10.3 mL, 108.2 mmol). The mixture is stirred for 10 min and then quenched with 1 N HCl. The solution is extracted with EtOAc and washed with 1 N HCl (3×) and sat. NaCl. The organic layer is dried over Na2SO4, filtered and concentrated. The residue is recrystallized from EtOAc to afford [(3-benzyloxy-7-bromonaphthalen-2-yl)-tert-butoxycarbony-amino]-acetic acid methyl ester.

Workup

  1. customquenched with 1 N HCl
  2. extractionThe solution is extracted with EtOAc
  3. washwashed with 1 N HCl (3×) and sat. NaCl
  4. dry with materialThe organic layer is dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is recrystallized from EtOAc

Sources & evidence

ORD record
ord-b7caaa4971aa49c1bbe8c2d8700ffc98
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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