Triethylamine → Cbz-L-Phenylalaninal

HRID 1422058Notes

Reaction equation

HRID 1422058 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:20][OH:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C>ClCCl.CS(C)=O.[Cl-].[Na+].O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH:20]=[O:21])[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 853481N-carbobenzoxy-L-phenylalanilol

Product 1

HCID 7021150Cbz-L-Phenylalaninal

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
15 °C

Procedure

To a solution of the objective compound (10.7 g, 37.5 mmol) of Step (1) and triethylamine (21.3 mL, 153 mmol) in dichloromethane (100 mL) was added a solution of sulfur trioxide-pyridine complex (23.9 g, 150 mmol) in dimethyl sulfoxide (DMSO) (100 mL) at -10° C. The obtained solution was stirred at 10-20° C. for 45 min and added to the saturated brine (400 mL). The mixture was extracted with ether. The extract was washed successively with 1 N hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure to give N-benzyloxycarbonyl-L-phenylalaninal as a white solid (0.6 g, quantitatively).

Workup

  1. extractionThe mixture was extracted with ether
  2. washThe extract was washed successively with 1 N hydrochloric acid
  3. dry with materiala saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a5626c621fd0407d9cfe8c6b21f677f9
Source dataset
uspto-grants-2000_06
Patent number
US06080738

Reaction notes

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