Dichloromethane → Phenylalanine, N-t-butyloxycarbonyl-4-nitro-, t-butyl ester

HRID 1861912노트

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HRID 1861912 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.[C:26](O)([CH3:29])([CH3:28])[CH3:27].Cl.C(N=C=NCCCN(C)C)C>C(OCC)(=O)C>[C:26]([O:11][C:10](=[O:12])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)([CH3:29])([CH3:28])[CH3:27]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 6386tert-ButanolHCID 1180712-tert-Butoxycarbonylamino-3-(4-nitro-phenyl)-propionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 546503Phenylalanine, N-t-butyloxycarbonyl-4-nitro-, t-butyl ester수율 97%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of the compound (6.9 g) obtained in Example 63 and methylene chloride (70 ml) were added t-butanol (20 ml), N,N-dimethylaminopyridine (2.63 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (4.9 g) and the resulting mixture was stirred at room temperature for 4 days. The reaction mixture was diluted with ethyl acetate and washed successively with 2 N HCl and a saturated aqueous sodium chloride solution; the organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=3:1) to give 7.64 g of the titled compound (yield, 97%).

후처리

  1. washwashed successively with 2 N HCl
  2. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=3:1)

출처 및 근거

ORD 기록
ord-ff96db7c8e374413b724973db09f5f77
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06534546B1

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