Acetonitrile → HCID 70135263, compound

HRID 1584670Notes

Reaction equation

HRID 1584670 reaction equation
C(O[C:9](=[O:26])[CH2:10][N:11]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C1C=CC=CC=1.[C:27](#[N:29])[CH3:28].[NH2-].[Na+].[CH2:32]([Mg]Cl)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CC(OC)(C)C>[NH2:29][C:27]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[CH:28][C:9](=[O:26])[CH:10]([N:11]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24533Sodium amideHCID 4683020Glycine, N,N-bis(phenylMethyl)-, phenylMethyl esterHCID 178418336HCID 178418336, compound

Product 1

HCID 70135263HCID 70135263, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

The title compound was prepared from N,N-dibenzyl-glycine benzyl ester, 113 mmole, and 6.5 mL, 125 mmole of acetonitrile. Following the procedure described in Example 2 the ester and nitrile mixture was added to 9.8 g, 225 mmole of sodium amide in MTBE. After solvent removal, benzyl magnesium chloride (PhCH2MgCl 250 mmole) was added following the procedure in Example 2. The resulting enamine was purified by chromatography, following the procedure described in Example 4. The yield of enamine was 41 g (102 mmole, 90%).

Workup

  1. additionwas added
  2. customThe resulting enamine was purified by chromatography

Sources & evidence

ORD record
ord-b2d69c283a9c495b820e3751dcd5cc62
Source dataset
uspto-grants-1999_08
Patent number
US05932766

Reaction notes

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