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

HRID 16325

反応式

HRID 16325 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). This reaction solution was stirred at room temperature for 1 hr. Then, ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The obtained organic layer was 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 obtained 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 organic layer was separated
  2. washThe obtained organic layer was washed with saturated saline twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionTo the obtained residue, diethylether was added
  6. customThe insoluble matter was removed by filtration
  7. concentrationthe filtrate was concentrated
  8. customThe obtained residue was purified by silica gel column chromatography (toluene ethyl acetate=6:1)

出典と根拠

ORDレコード
ord-c79eca467f9347519f110d1079b2558d
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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