Hydrochloric Acid → Z-FF-Fmk

HRID 248589

반응식

HRID 248589 반응식
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN1CCOCC1.[NH2:30][C@H:31]([C:39]([CH2:41][F:42])=[O:40])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl.Cl>C1COCC1.CN(C=O)C>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([NH:30][C@H:31]([C:39]([CH2:41][F:42])=[O:40])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 79724-Methylmorpholine2회HCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 131717227PheCH2F hydrochloride

생성물 1

HCID 11705307Z-FF-Fmk

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of Z-PheOH (0.207 g, 0.69 mmol) in THF (4 mL), cooled to -20° C., were added NMM (76 uL, 0.69 mmol) and IBCF (90 uL, 0.69 mmol). After 10 minutes, a chilled (-10° C.) solution of PheCH2F hydrochloride (0.15 g, 0.69 mmol) in DMF (1 mL) was added, followed by NMM (76 uL, 0.69 mmol). The mixture was stirred for 30 minutes. 1M HCl (5 mL) was added. The solution was extracted with ethyl acetate (30 mL), washed with saturated aqueous NaHCO3 (6 mL), brine (4 mL), dried over MgSO4, filtered, and evaporated to dryness. The residue was crystallized from ethyl acetate/hexane, yielding 0.22 (53%) of Z-Phe-PheCH2F.

후처리

  1. additionwas added
  2. extractionThe solution was extracted with ethyl acetate (30 mL)
  3. washwashed with saturated aqueous NaHCO3 (6 mL), brine (4 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was crystallized from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-b056866b65314ff4a2dd2e3080fdd500
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05210272

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