Cornforth reagent → Methyl 4-[bis(tert-butoxy)phosphorylcarbonyl]-N-(benzyloxycarbonyl)-D,L-phenylalaninate

HRID 258169노트

반응식

HRID 258169 반응식
[C:1]([O:5][P:6]([CH:13]([OH:37])[C:14]1[CH:36]=[CH:35][C:17]([CH2:18][CH:19]([C:31]([O:33][CH3:34])=[O:32])[NH:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])=[CH:16][CH:15]=1)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)(Cl)Cl.CCOC(C)=O>[C:9]([O:8][P:6]([C:13]([C:14]1[CH:36]=[CH:35][C:17]([CH2:18][CH:19]([C:31]([O:33][CH3:34])=[O:32])[NH:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])=[CH:16][CH:15]=1)=[O:37])([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])([CH3:10])([CH3:11])[CH3:12]

참가 물질

5

반응물 2

HCID 2724130Cornforth reagentHCID 10392366Methyl 4-[bis(tert-butoxy)phosphorylhydroxymethyl]-N-(benzyloxycarbonyl)-D,L-phenylalaninate

생성물 1

HCID 11756879Methyl 4-[bis(tert-butoxy)phosphorylcarbonyl]-N-(benzyloxycarbonyl)-D,L-phenylalaninate수율 70%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 9 (125 mg, 0.23 mmol) in CHCl3 (1 mL) was added celite (200 mg) and freshly activated 4A molecular sieves (230 mg). Pyridinium dichromate (219 mg, 0.58 mmol) was added and the mixture stirred at ambient temperature (4 hours). The reaction was diluted with EtOAc (5 mL) and filtered through a pad of Florisil (TLC grade). The Florisil was rinsed with EtOAc (30 mL) and combined filtrates taken to dryness by rotary evaporation under reduced pressure to afford crude 10 (85 mg, 70%). Silica gel chromatography [EtOAc/hexanes (1:1)]provided pure 10 (77 mg, 62%).

후처리

  1. filtrationfiltered through a pad of Florisil (TLC grade)
  2. washThe Florisil was rinsed with EtOAc (30 mL)
  3. customtaken to dryness by rotary evaporation under reduced pressure

출처 및 근거

ORD 기록
ord-87e1d5322a49400ebf043d4eb1d7d592
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05264607

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