Methanol → tert-butyl [(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamate

HRID 16356

反応式

HRID 16356 の反応式
C(=O)([O-])[O-].[K+].[K+].CO.C1COCC1.[C:14]([O:18][C:19]([NH:21][C@H:22]([C:37]1[CH:42]=[C:41]([F:43])[C:40]([F:44])=[C:39]([F:45])[CH:38]=1)[C@H:23]([O:25]C(=O)C1C=CC([N+]([O-])=O)=CC=1)[CH3:24])=[O:20])([CH3:17])([CH3:16])[CH3:15]>O.C(OCC)(=O)C>[C:14]([O:18][C:19](=[O:20])[NH:21][C@H:22]([C:37]1[CH:42]=[C:41]([F:43])[C:40]([F:44])=[C:39]([F:45])[CH:38]=1)[C@H:23]([OH:25])[CH3:24])([CH3:15])([CH3:16])[CH3:17]

参加物

7

反応物 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 68911294[(1R,2R)-2-tert-butoxycarbonylamino-1-methyl-2-(3,4,5-trifluorophenyl)ethyl]4-nitrobenzoate

生成物 1

HCID 68717986tert-butyl [(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamate収率 95.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A potassium carbonate powder (6.43 g) was added to a solution mixture of methanol (90 mL) and THF (10 mL) of 4-nitrobenzoic acid (1R,2R)-2-tert-butoxycarbonylamino-1-methyl-2-(3,4,5-trifluorophenyl)ethyl ester (7.03 g). The resulting reaction solution was stirred at room temperature for 1 hr, and ethyl acetate and water were added thereto. The organic layer was separated, washed with saturated saline twice, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the obtained residue, diethylether was added. The insoluble matter was removed by filtration, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (toluene:ethyl acetate=6:1) to give 4.49 g of the title compound. The physical property values of this compound were as follows:

後処理

  1. customThe resulting reaction solution
  2. customThe organic layer was separated
  3. washwashed with saturated saline twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the obtained residue, diethylether was added
  7. customThe insoluble matter was removed by filtration
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified by silica gel column chromatography (toluene:ethyl acetate=6:1)

出典と根拠

ORDレコード
ord-a8f4e62a5cd14e3b94a24f41ed5e48fb
出典データセット
uspto-grants-2010_06
特許番号
US07737141B2

関連ノート

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