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4-Methylmorpholine → N-[2-(Diethoxyphosphinyl)-3-(4-methoxyphenyl) propionyl]-L-leucine, tert-butyl ester

HRID 905360
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HRID 905360 반응식
[CH2:1]([O:3][P:4]([O:19][CH2:20][CH3:21])([CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[C:7]([OH:9])=O)=[O:5])[CH3:2].CN1CCOCC1.C(OC(Cl)=O)C(C)C.[C:37]([O:41][C:42](=[O:49])[C@H:43]([CH2:45][CH:46]([CH3:48])[CH3:47])[NH2:44])([CH3:40])([CH3:39])[CH3:38]>C1COCC1.CN(C=O)C>[CH2:20]([O:19][P:4]([O:3][CH2:1][CH3:2])([CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[C:7]([NH:44][C@H:43]([C:42]([O:41][C:37]([CH3:39])([CH3:38])[CH3:40])=[O:49])[CH2:45][CH:46]([CH3:48])[CH3:47])=[O:9])=[O:5])[CH3:21]
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참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 7022311tert-butyl (2S)-2-amino-4-methylpentanoateHCID 131383212-(Diethoxyphosphinyl)-3-(4-methoxyphenyl)propionic acid

생성물 1

HCID 13138324N-[2-(Diethoxyphosphinyl)-3-(4-methoxyphenyl) propionyl]-L-leucine, tert-butyl ester

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8028Tetrahydrofuran용매

반응 조건

온도
-15 °C

실험 절차

The product of stage (b) was dissolved in THF (20 ml), cooled to -25° C. and with stirring NMM (1.28 g) and then isobutylchloroformate (1.65 g) successively added. After two minutes, a precooled solution of leucine tert-butyl ester (2.15 g) in DMF (5 ml) was added and the mixture stirred at -15° C. for 2 hr. The temperature was raised to 0° C. and stirring continued for 0.5 hr after the addition of 2 M KHCO3 (14 ml). The product was evaporated in vacuo, the residue suspended in ethyl acetate and succesively washed with 5% citric acid, 10% NaHCO3 and brine, dried (MgSO4) and concentrated to a white solid, m.p. 80°-87° (dec). The structure was confirmed by NMR and the product was used in the next stage without further purification.

후처리

  1. temperatureThe temperature was raised to 0° C.
  2. stirringstirring
  3. waitcontinued for 0.5 hr
  4. customThe product was evaporated in vacuo
  5. washsuccesively washed with 5% citric acid, 10% NaHCO3 and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated to a white solid, m.p. 80°-87° (dec)
  8. customthe product was used in the next stage without further purification

출처 및 근거

ORD 기록
ord-3b5744c932734a76964bf41ddab0465b
출처 데이터셋
uspto-grants-1983_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04423242

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