Acetonitrile → HCID 70133040, compound

HRID 1584669Notes

Reaction equation

HRID 1584669 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])[CH2:10][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

Participants

6

Reactant 4

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

Product 1

HCID 70133040HCID 70133040, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

The title compound was prepared from N,N-dibenzyl-glycine benzyl ester, 54 mmole, and 3.3 mL, 64 mmole of acetonitrile. Following the procedure described in Example 2 the ester and nitrile mixture was added to 5.5 g, 127 mmole of sodium amide in MTBE. After solvent removal, benzyl magnesium chloride (PhCH2MgCl 145 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 22.3 g (50 mmole, 78%).

Workup

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

Sources & evidence

ORD record
ord-e1a3f166e29044b39a9dbf6ecb2f6839
Source dataset
uspto-grants-1999_08
Patent number
US05932766

Reaction notes

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