Dichloromethane → N-(tert-Butoxycarbonyl)-N-ethyl-L-phenylalanine

HRID 1980472Notes

Reaction equation

HRID 1980472 reaction equation
C([O:3][C:4](=[O:23])[C@H:5]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][CH3:8])C.[OH-].[K+].ClCCl.S(=O)(=O)(O)[O-].[Na+]>O1CCCC1.O>[C:12]([O:11][C:9]([N:6]([CH2:7][CH3:8])[C@H:5]([C:4]([OH:23])=[O:3])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:10])([CH3:14])([CH3:15])[CH3:13]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 516919Sodium BisulfateHCID 13502055HCID 13502055, compound

Product 1

HCID 13049159N-(tert-Butoxycarbonyl)-N-ethyl-L-phenylalanine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 16 g (0.05 mole) of t-butoxycarbonyl-N-ethylphenylalanine ethyl ester (prepared as in Example 11) in 200 ml of tetrahydrofuran was added 6.6 g (0.1 mole) of potassium hydroxide in 400 ml of water. After the mixture was stirred overnight, 400 ml of dichloromethane was added and the mixture acidified to pH 3 with 0.5M sodium bisulfate. The aqueous layer was separated and washed with dichloromethane, and all organic layers were recombined. This organic solution was further washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo to dryness. Column chromatography on silica gel afforded 10.9 g of the analytically pure title compound.

Workup

  1. customThe aqueous layer was separated
  2. washwashed with dichloromethane
  3. washThis organic solution was further washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-4c98548b9e7e438db0da6797392bae93
Source dataset
uspto-grants-1985_04
Patent number
US04510085

Reaction notes

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