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

HRID 1280631

반응식

HRID 1280631 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-25 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c736a33b2aac4d26a0be6a08abde5601
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06451821B1

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