Sodium hydride → HCID 66756895, compound

HRID 475412Notes

Reaction equation

HRID 475412 reaction equation
C([O:8][C:9](=O)[C@@H:10]([CH3:19])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])C1C=CC=CC=1.[C:21]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(=[O:34])/[CH:22]=[CH:23]/[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25].[H-].[Na+]>C1(C)C=CC=CC=1.C(OCC)C>[C:15]([O:14][C:12]([N:11]1[CH:10]([CH3:19])[C:9](=[O:8])[CH:23]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH:22]1[C:21]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 2829312538-64-7HCID 11027083HCID 11027083, compound

Product 1

HCID 66756895HCID 66756895, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5.59 g (20.0 mmol) of (R)—N-tert-butoxycarbonylalanine benzyl ester and 5.92 g (20.0 mmol) of dibenzyl fumarate in 60 mL of toluene was added 1.60 g (40 mmol) of 60% NaH in mineral oil. The reaction was stirred at ambient temperature under N2 for 24 h, then diluted with 300 mL of diethyl ether. The solution was extracted with 1M HCl(aq.) (1×50 mL), saturated NaHCO3(aq.) (3×50 mL), and brine (1×50 mL), dried over MgSO4, filtered, and concentrated to provide the titled compound as an oil.

Workup

  1. extractionThe solution was extracted with 1M HCl(aq.) (1×50 mL), saturated NaHCO3(aq.) (3×50 mL), and brine (1×50 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-284e3fc06ec144fcb86ff6bd403a2927
Source dataset
uspto-grants-2014_01
Patent number
US08637546B2

Reaction notes

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