Sodium hydride → HCID 59516112, compound

HRID 1799414Notes

Reaction equation

HRID 1799414 reaction equation
[H-].[Na+].[NH:3]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[NH:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].Br[CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1>C1COCC1>[CH3:16][C:15]([O:14][C:12]([N:3]([CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1)[NH:4][C:5]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:6])=[O:13])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 85431Di-tert-butyl bicarbamateHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 59516112HCID 59516112, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

NaH (362 mg, 9.04 mmol) was added to a stirred solution of Di-Tert-Butyl Hydrazodicarboxylate (2 g, 8.61 mmol) in anhydrous THF (50 ml). The reaction was stirred at ambient temperature for 10 minutes then treated with a solution of Methy 4-(Bromomethyl)Benzoate (1.98 g, 8.61 mmol) in anhydrous THF (20 ml). The reaction was stirred at ambient temperature for 4 hours. The reaction was partitioned between ether (˜100 ml) and water (˜100 ml). The layers were separated and the aqueous layer was re-extracted with ether (˜50 ml). The ether layers were combined, washed with brine (˜50 ml), dried (MgSO4), filtered and evaporated to yield the title compound (3.3 g, 100%).

Workup

  1. stirringThe reaction was stirred at ambient temperature for 4 hours
  2. customThe reaction was partitioned between ether (˜100 ml) and water (˜100 ml)
  3. customThe layers were separated
  4. extractionthe aqueous layer was re-extracted with ether (˜50 ml)
  5. washwashed with brine (˜50 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-fab559be9f504da080681a0653176a78
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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