Hydrochloric Acid → Boc-homophenylalaninal

HRID 1600525

반응식

HRID 1600525 반응식
N1(C(N[C@H](C(O)=O)[CH2:11][C:12]2[CH:17]=CC=C[CH:13]=2)=O)CCOCC1.CN1CC[O:25]CC1.Cl[C:29]([O:31]CC(C)C)=[O:30].Cl.[NH2:37][C@@H:38]([CH2:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH:39]=CC(OCC)=O.Cl>C1COCC1.CN(C=O)C>[C:29]([NH:37][C@H:38]([CH:39]=[O:25])[CH2:46][CH2:47][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)([O:31][C:12]([CH3:11])([CH3:13])[CH3:17])=[O:30]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 79724-Methylmorpholine2회HCID 62365Isobutyl chloroformateHCID 664657CP 84364HCID 86754733ethyl (S)-4-amino-6-phenyl-2-hexenoate hydrochloride

생성물 1

HCID 10264740Boc-homophenylalaninal수율 80%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

Morpholinecarbonylphenylalanine (2.74 g, 9.82 mmol, prepared according to the method described in Esser, R. et.al., Arthritis & Rheumatism (1994), 0000) was dissolved in THF (50 mL) at -10° C. 4-methylmorpholine (1.08 mL, 9.82 mmol) was added, followed by isobutyl chloroformate (1.27 mL, 9.82 mmol). The mixed anhydride was stirred for 10 minutes, whereupon a solution of ethyl (S)-4-amino-6-phenyl-2-hexenoate hydrochloride from the previous step in DMF (10 mL) was added, followed by 4-methylmorpholine (1.08 mL, 9.82 mmol). The mixture was stirred for 1 hour. 1M HCl (50 mL) was added. The product was extracted with ethyl acetate (100 mL), washed with saturated aqueous NaHCO3 (50 mL), dried over MgSO4 and decolorizing charcoal (DARCO), filtered, and evaporated to dryness, giving 3.80 g (80% yield from Boc-homophenylalaninal).

후처리

  1. additionwas added
  2. extractionThe product was extracted with ethyl acetate (100 mL)
  3. washwashed with saturated aqueous NaHCO3 (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness

출처 및 근거

ORD 기록
ord-acf3b734ba6c4d49893738d6d94827e3
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05976858

연결된 노트

불러오는 중…