L-Alanine → HCID 29891930, compound

HRID 586151Notes

Reaction equation

HRID 586151 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].C(N(CC)CC)C.C[Si](Cl)(C)C.[CH:19]1([C:24](Cl)=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20]1>ClCCl.O>[CH:19]1([C:24]([NH:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3])=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 5950L-AlanineHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 78284Cyclopentanecarbonyl chloride

Product 1

HCID 29891930HCID 29891930, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Alanine (16.8 g, 189 mmol) and 57.8 ml (415 mmol) of triethylamine are dissolved in 200 ml of dichloromethane and 52.7 ml (415 mmol) of trimethylsilyl chloride are added dropwise. After addition is complete, the mixture is stirred for 1 h at room temperature and for 1 h at 40° C. After this, the batch is cooled to −10° C. and cyclopentanecarbonyl chloride (25.0 g, 189 mmol) is added dropwise and the mixture is stirred at this temperature for 2 h. The reaction mixture is treated with 100 ml of water with cooling, stirred for 10 min and and filtered with suction. The residue is washed with water and diethyl ether and dried at 60° C.

Workup

  1. additionAfter addition
  2. temperatureAfter this, the batch is cooled to −10° C.
  3. stirringthe mixture is stirred at this temperature for 2 h
  4. temperaturewith cooling
  5. stirringstirred for 10 min
  6. filtrationfiltered with suction
  7. washThe residue is washed with water and diethyl ether
  8. customdried at 60° C.

Sources & evidence

ORD record
ord-e8804247927f4cb88648fd62a4cf111a
Source dataset
uspto-grants-2005_08
Patent number
US06936609B2

Reaction notes

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