Glycine tert-butyl ester → HCID 76476580, compound

HRID 1982627Notes

Reaction equation

HRID 1982627 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7][NH2:8])([CH3:4])([CH3:3])[CH3:2].[CH3:10][CH:11]([CH3:26])[CH2:12][CH:13]1[CH2:15][N@@:14]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C(O)C>[CH3:26][CH:11]([CH3:10])[CH2:12][CH:13]([NH:14][C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])[CH2:15][N:8]([CH2:15][CH:13]([NH:14][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[CH2:12][CH:11]([CH3:10])[CH3:26])[CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:9]

Participants

4

Reactant 2

HCID 151417Glycine tert-butyl esterHCID 85524729HCID 85524729, compound

Product 1

HCID 76476580HCID 76476580, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A refluxing solution of 15.1 g (a 10% excess) of glycine t-butyl ester in 200 ml of absolute ethanol is treated dropwise over one hour with a solution of 24.2 g of (S)-2-(2-methylpropyl)-1-aziridinecarboxylic acid, phenylmethyl ester in 50 ml of absolute ethanol. The refluxing is continued over two nights. The solvent is removed under reduced pressure and the residue chromatographed on 1.5 kg of silica gel, eluting with chloroform/ethylacetate (3:1). Combining the fractions containing the faster eluting compound gives 14.3 g of an oil which crystallizes on standing. A small example, recrystallized from hexane has mp 107°-108°, [α]D23 -16.3° (c 1.03, methanol). Spectral and elemental analysis shows this to be [S-(R*,R*)]-N,N-bis[4-methyl-2-[[(phenylmethoxy)carbonyl]amino]pentyl]glycine, 1,1-dimethylethyl ester.

Workup

  1. waitThe refluxing is continued over two nights
  2. customThe solvent is removed under reduced pressure
  3. customthe residue chromatographed on 1.5 kg of silica gel
  4. washeluting with chloroform/ethylacetate (3:1)
  5. additioncontaining the
  6. washfaster eluting compound

Sources & evidence

ORD record
ord-2c56175848834f838f614384a1f4a364
Source dataset
uspto-grants-1986_06
Patent number
US04596819

Reaction notes

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