Methyl chloroformate → HCID 70073510, compound

HRID 1977586Notes

Reaction equation

HRID 1977586 reaction equation
[NH2:1][C@@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:14]([O:16][CH3:17])=[O:15].[CH:18]1([NH:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>[OH-].[Na+].O>[CH:25]1([NH:24][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1.[CH3:17][O:16][C:14]([NH:1][C@@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:15]

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 7582DicyclohexylamineHCID 71567D-Phenylalanine

Product 1

HCID 70073510HCID 70073510, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
0 °C

Procedure

5 g (30 mmol) of D-phenylalanine is dissolved in 15 ml of 2M NaOH solution, cooled to 0° C. and, simultaneously, 16.5 ml of 2M NaOH solution and 2.55 ml (33 mmol) of methyl chloroformate are added. The mixture is stirred at this temperature for 30 min, then at room temperature for 2 hours. Diluted with 40 ml of water, the mixture is washed with 10 ml of diethyl ether, acidified to pH3 with 3M HCl and extracted with 4×20 ml of ethyl acetate. The pooled organic extracts are washed with water (20 ml), dried over anhydrous sodium sulphate and evaporated at a pressure of 2.0-2.5 kPa. The residue is dissolved in 60 ml of diisopropyl ether and 6 ml (30 mmol) of dicyclohexylamine is added. The separated crystals are filtered off, washed with diisopropyl ether and dried in air.

Workup

  1. waitat room temperature for 2 hours
  2. washthe mixture is washed with 10 ml of diethyl ether
  3. extractionextracted with 4×20 ml of ethyl acetate
  4. washThe pooled organic extracts are washed with water (20 ml)
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated at a pressure of 2.0-2.5 kPa
  7. dissolutionThe residue is dissolved in 60 ml of diisopropyl ether
  8. filtrationThe separated crystals are filtered off
  9. washwashed with diisopropyl ether
  10. customdried in air

Sources & evidence

ORD record
ord-65654ccdf982421a9ac2b8092ab44993
Source dataset
uspto-grants-2001_05
Patent number
US06235707B1

Reaction notes

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