Ethanol → ethyl (2R)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate

HRID 1280631Notes

Reaction equation

HRID 1280631 reaction equation
S(Cl)(Cl)=O.[NH2:5][C@H:6]([CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C:7]([OH:9])=[O:8].[CH2:25](O)[CH3:26]>C(OCC)(=O)C.CO>[NH2:5][C@H:6]([CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C:7]([O:9][CH2:25][CH3:26])=[O:8]

Participants

6

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 1551330H-D-Lys(Z)-OH

Product 1

HCID 86584429ethyl (2R)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-25 °C

Procedure

3.9 cm3 of thionyl chloride are added to a stirred suspension of 7.9 g of (2R)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoic acid (Ns-CBZ-D-lysine) in 120 cm3 of anhydrous ethanol cooled to a temperature in the region of −25° C. The mixture is stirred for 3 hours at this temperature and is then allowed to warm to about 20° C. After leaving for 3 days, the reaction mass is concentrated under reduced pressure (5 kPa) at a temperature in the region of 0° C. The residue obtained is taken up in 200 cm3 of ethyl acetate and the resulting solution is washed with aqueous sodium carbonate solution and then with aqueous sodium chloride solution. The organic solution is dried over magnesium sulfate, filtered and concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 7.4 g of ethyl (2R)-2-amino-6-{[(benzyloxy)-=carbonyl]amino}hexanoate are obtained in the form of a pale yellow oil. (αD20=−11.7±0.6 at a concentration of 0.5% in methanol).

Workup

  1. temperatureto warm to about 20° C
  2. customAfter leaving for 3 days
  3. concentrationthe reaction mass is concentrated under reduced pressure (5 kPa) at a temperature in the region of 0° C
  4. customThe residue obtained
  5. washthe resulting solution is washed with aqueous sodium carbonate solution
  6. dry with materialThe organic solution is dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  9. custom7.4 g of ethyl (2R)-2-amino-6-{[(benzyloxy)-=carbonyl]amino}hexanoate are obtained in the form of a pale yellow oil

Sources & evidence

ORD record
ord-c736a33b2aac4d26a0be6a08abde5601
Source dataset
uspto-grants-2002_09
Patent number
US06451821B1

Reaction notes

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