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

HRID 258169ノート

反応式

HRID 258169 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-87e1d5322a49400ebf043d4eb1d7d592
出典データセット
uspto-grants-1993_11
特許番号
US05264607

反応ノート

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