L-Phenylalanine → L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-L-leucyl-

HRID 2419489노트

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HRID 2419489 반응식
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CCN(CC)CC.[NH:20]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C@H:21]([C:26](OC1C(F)=C(F)C(F)=C(F)C=1F)=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24]>CN(C=O)C>[NH:20]([C:40]([O:42][C:43]([CH3:45])([CH3:44])[CH3:46])=[O:41])[C@H:21]([C:26]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24]

참가 물질

5

반응물 3

HCID 6140L-PhenylalanineHCID 8471TriethylamineHCID 11047584HCID 11047584, 화합물

생성물 1

HCID 10981745L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-L-leucyl-

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

H-Phe-OH (1.49 g, 9 mmol) fine powder was suspended in DMF (20 ml). After cooling at 0°, Et3N (1.26 ml, 9 mmol) was added, followed by Boc-Leu-pentafluorophenylester, i.e., Boc-Leu-OPfp (3.93 g, 9.9 mmol). It was stirred for 1 hr at 0° C and for 2.5 hr at room temperature. After filtration the solvent was evaporated and the residue was treated with H2O. The separated oil was extracted with EtOAc. The organic phase was washed with 10% citric acid, H2O, dried (Na2SO4) and evaporated to a smaller volume. Addition of petroleum ether and standing overnight in the refrigerator provided the product (XVI) which was recrystallized from EtOAc-petroleum ether to fine crystals, yield 2.3 g (67.6%); mp 104°-106° C; [α]D25 -3.40° (c 1, EtOH). Anal. Calcd for C20H30N2O5 (378.476): C, 63.47; H, 7.99; N, 7.40. Found: C, 63.46; H, 8.18; N, 7.49.

후처리

  1. temperatureAfter cooling at 0°
  2. filtrationAfter filtration the solvent
  3. customwas evaporated
  4. additionthe residue was treated with H2O
  5. extractionThe separated oil was extracted with EtOAc
  6. washThe organic phase was washed with 10% citric acid, H2O
  7. dry with materialdried (Na2SO4)
  8. customevaporated to a smaller volume
  9. additionAddition of petroleum ether
  10. waitstanding overnight in the refrigerator

출처 및 근거

ORD 기록
ord-c9bc524b711c461ea6537a05c40a94cb
출처 데이터셋
uspto-grants-1978_08
특허 번호
US04105652

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