{(1R,2R)-2-benzyloxy-1-[(methoxymethylcarbamoyl)methoxymethyl]propyl}carbamic acid t-butyl ester → {(1R,2R)-2-benzyloxy-1-[2-(4-chlorophenyl)-2-oxoethoxymethyl]propyl}carbamic acid t-butyl ester

HRID 16375

反応式

HRID 16375 の反応式
[C:1]([O:5][C:6](=[O:28])[NH:7][C@H:8]([CH2:19][O:20][CH2:21][C:22](=[O:27])NCOC)[C@H:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:10])([CH3:4])([CH3:3])[CH3:2].[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([Mg]Br)=[CH:32][CH:31]=1>O1CCCC1.[Cl-].[NH4+]>[C:1]([O:5][C:6](=[O:28])[NH:7][C@H:8]([CH2:19][O:20][CH2:21][C:22]([C:33]1[CH:34]=[CH:35][C:30]([Cl:29])=[CH:31][CH:32]=1)=[O:27])[C@H:9]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH3:10])([CH3:2])([CH3:3])[CH3:4]

参加物

5

反応物 2

HCID 67379173{(1R,2R)-2-benzyloxy-1-[(methoxymethylcarbamoyl)methoxymethyl]propyl}carbamic acid t-butyl esterHCID 178478191HCID 178478191、化合物

生成物 1

HCID 67373088{(1R,2R)-2-benzyloxy-1-[2-(4-chlorophenyl)-2-oxoethoxymethyl]propyl}carbamic acid t-butyl ester

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
0 °C

実験手順

A solution of {(1R,2R)-2-benzyloxy-1-[(methoxymethylcarbamoyl)methoxymethyl]propyl}carbamic acid t-butyl ester (2.42 g) in tetrahydrofuran (50 mL) was cooled to −40° C. and to the mixture was then dropwise added 4-chlorophenylmagnesium bromide (18.3 mL, 1 M tetrahydrofuran solution). The resultant solution was stirred for 1 hour at −40° C., after which the temperature was slowly raised to 0° C. The solution was then diluted with saturated aqueous ammonium chloride. The resultant solution was extracted using ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. Solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate 9/1→1/1), to thereby obtain the titled compound (2.61 g). The physical properties of this crude product were as follows.

後処理

  1. extractionThe resultant solution was extracted
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customSolvent was removed by distillation under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate 9/1→1/1)

出典と根拠

ORDレコード
ord-4c957e16d1a84e578fc1b0ae8c2d812d
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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