DL-alanine → HCID 22324207, compound

HRID 495989Notes

Reaction equation

HRID 495989 reaction equation
[NH2:1][CH:2]([C:4]([OH:6])=O)[CH3:3].[CH2:7](N(CC)CC)[CH3:8].C[Si](Cl)(C)C.[CH2:19]([CH:21](CC)[C:22](Cl)=[O:23])[CH3:20].[OH-:27].[Na+]>ClCCl.O>[CH3:7][CH2:8][C:2]([NH:1][C:22](=[O:23])[CH2:21][CH2:19][CH3:20])([CH3:3])[C:4]([OH:6])=[O:27]

Participants

8

Reactant 5

HCID 602DL-alanineHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 759542-Ethylbutyryl chloride

Product 1

HCID 22324207HCID 22324207, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

24.5 g (0.275 mol) of D,L-alanine are initially charge in 250 ml of dichloromethane, and 61.2 g (0.605 mol) of triethylamine are added. The mixture is cooled to 0° C. and 65.7 g (0.605 mol) of trimethylsilyl chloride are added. The mixture is stirred at room temperature for 1 hour and at 40° C. for 1 hour. The mixture is cooled to −10° C., and 37 g (0.275 mol) of 2-ethylbutyryl chloride are added dropwise. The mixture is stirred at −10° C. for 2 hours and at room temperature overnight. The mixture is cooled in an ice-bath and 150 ml of water are added dropwise. 50 g (1.25 mol) of NaOH dissolved in 100 ml of water, are added, and the aqueous phase is separated off and concentrated. The residue is again taken up in water and acidified with concentrated hydrochloric acid, the aqueous solution is extracted repeatedly with dichloromethane and the organic phase is dried over Na2SO4 and concentrated.

Workup

  1. temperatureThe mixture is cooled to −10° C.
  2. stirringThe mixture is stirred at −10° C. for 2 hours and at room temperature overnight
  3. temperatureThe mixture is cooled in an ice-bath
  4. additionare added
  5. customthe aqueous phase is separated off
  6. concentrationconcentrated
  7. extractionthe aqueous solution is extracted repeatedly with dichloromethane
  8. dry with materialthe organic phase is dried over Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-26c31a41944c479ea4f412fbbae5ac12
Source dataset
uspto-grants-2005_09
Patent number
US06943163B2

Reaction notes

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