Benzyloxycarbonyl-L-phenylalanine → N-benzyloxycarbonylphenylalanine methyl ester

HRID 506764노트

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HRID 506764 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:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:23]CN=C=NCCCN(C)C.Cl>CO.CN(C1C=CN=CC=1)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]([O:12][CH3:23])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

참가 물질

5

반응물 2

HCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 3082435N-benzyloxycarbonylphenylalanine methyl ester

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 887Methanol용매

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온도
4 °C

실험 절차

After 1.80 g of Z-Phe was dissolved in 20 mL of MeOH, 73 mg of DMAP, 1.38 g of WSCD HCl were added at 0° C., followed by stirring at 4° C. for 12 hours. The solvent was concentrated and the concentrate was dissolved in AcOEt, followed by washing with 1N HCl aq., satd. NaHCO3 aq., and satd. NaCl aq. After drying over Na2SO4, the solvent was concentrated to give Z-Phe-OMe as oil. After dissolving in 20 mL of dry THF, 196 mg of LiBH4 was added thereto and the mixture was stirred at room temperature for 15 hours. The solvent was concentrated and the concentrate was dissolved in AcOEt and the residue was washed with 1N HCl aq., satd. NaHCO3 aq., and satd. NaCl aq. After drying over Na2SO4, the solvent was concentrated and ether-petroleum ether was added to give 1.45 g (yield 85%) of Z-Phe-ol as precipitates. After 60 mg of 60% NaH was suspended in 10 mL of dry THF, 285 mg of Z-Phe-ol, 264 mg of 18-crown-6 and 1.48 mL of tert-butyl bromoacetate were added at 0° C. While returning to room temperature, the mixture was stirred for 15 hours.

후처리

  1. concentrationThe solvent was concentrated
  2. dissolutionthe concentrate was dissolved in AcOEt
  3. washby washing with 1N HCl aq.
  4. dry with materialNaCl aq. After drying over Na2SO4
  5. concentrationthe solvent was concentrated

출처 및 근거

ORD 기록
ord-f2143e23d4d84f948777d4fbe0de1cea
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786083B2

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