4-Methylmorpholine → Boc-AlaAlaPro-OBzl

HRID 1458178노트

반응식

HRID 1458178 반응식
Cl.[CH2:2]([O:9][C:10](=[O:21])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:20])[C@H:17]([CH3:19])[NH2:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CN1CCOCC1.[C:29]([NH:36][C@H:37]([C:39](O)=[O:40])[CH3:38])([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].C(ON1C2C(=CC=CC=2)CC(=C=O)C1OCC)C>C(Cl)Cl.O>[CH2:2]([O:9][C:10](=[O:21])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:20])[C@H:17]([CH3:19])[NH:18][C:39](=[O:40])[C@H:37]([CH3:38])[NH:36][C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 85082Tert-butoxycarbonylalanineHCID 13034412L-alanyl-L-proline, phenylmethyl ester, hydrochlorideHCID 867493291-Ethoxy-carbonyl-2-ethoxy-1,2-dihydroquinoline

생성물 1

HCID 15289361Boc-AlaAlaPro-OBzl수율 81.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

L-alanyl-L-proline benzyl ester hydrochloride (13.0 g, 41.6 mmol) was dissolved in methylene chloride (650 ml) under an argon atmosphere in a flask fitted with an over-head stirrer. N-methylmorpholine (4.8 ml, 43.6 mmol) was syringed into the solution and, after 5 minutes, Boc-L-alanine (7.9 g, 41.6 mmol) was added followed by 1-ethoxy-carbonyl-2-ethoxy-1,2-dihydroquinoline (11.8 g, 47.8 mmol). The resulting solution was stirred at room temperature overnight. The reaction mixture was poured into a separatory funnel containing water (300 ml) and the layers separated. The aqueous layer was extracted with chloroform (200 ml) and the combined organic extracts were washed with 0.5N hydrochloric acid (3×200 ml), water (2×200 ml), saturated sodium bicarbonate (2×200 ml) and brine (200 ml). The organic layer was then dried over magnesium sulfate, filtered and concentrated on a rotary evaporator. Addition of ether-hexane gave crude Boc-L-alanyl-L-alanyl-L-proline benzyl ester which could be recrystallized from ethyl acetate-hexane to give the pure product (15.1 g) mp 124°-126° C.

후처리

  1. customfitted with an over-head stirrer
  2. additionThe reaction mixture was poured into a separatory funnel
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with chloroform (200 ml)
  5. washthe combined organic extracts were washed with 0.5N hydrochloric acid (3×200 ml), water (2×200 ml), saturated sodium bicarbonate (2×200 ml) and brine (200 ml)
  6. dry with materialThe organic layer was then dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated on a rotary evaporator
  9. additionAddition of ether-hexane
  10. customgave crude Boc-L-alanyl-L-alanyl-L-proline benzyl ester which
  11. customcould be recrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-5bc1278c4a2a4e538a2b4850f28d6349
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05849866

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