Water → HCID 11418746、化合物

HRID 2098405ノート

反応式

HRID 2098405 の反応式
[CH:1]([C@H:4]([CH2:8]/[CH:9]=[CH:10]/[CH2:11][C@H:12]([C:16](=O)[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH2:26][CH2:27][CH2:28][O:29][CH3:30])[CH:18]=1)[CH:13]([CH3:15])[CH3:14])[C:5]([OH:7])=[O:6])([CH3:3])[CH3:2].C([SiH](CC)CC)C.O>FC(F)(F)C(O)=O>[CH:1]([C@H:4]([CH2:8]/[CH:9]=[CH:10]/[CH2:11][C@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH2:26][CH2:27][CH2:28][O:29][CH3:30])[CH:18]=1)[CH:13]([CH3:15])[CH3:14])[C:5]([OH:7])=[O:6])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 962WaterHCID 12052Triethylsilane2 回HCID 16660460HCID 16660460、化合物

生成物 1

HCID 11418746HCID 11418746、化合物収率 61%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

To a solution of (2S,7S)-trans-2-isopropyl-7-[4-methoxy-3-(3-methoxypropyloxy)-benzoyl]-8-methylnon-4-enoic acid (90 mg; 0.21 mmol) in trifluoroacetic acid (1 ml) was added triethylsilane (250 μl; 1.5 mmol). After stirring the solution at RT for 1 day, a second portion of triethylsilane (250 μl; 1.5 mmol) was added, and the solution was stirred at RT for a further 2 days and then added to water. The aqueous layer was extracted 3× with tert-butyl methyl ether and the organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude residue was purified by flash chromatography (silica gel; hexane/acetone 4:1) to obtain (2S,7R)-trans-2-isopropyl-7-[4-methoxy-3-(3-methoxypropoxy)benzyl]-8-methylnon-4-enoic acid (53 mg, 0.126 mmol, 61% yield).

後処理

  1. stirringthe solution was stirred at RT for a further 2 days
  2. extractionThe aqueous layer was extracted 3× with tert-butyl methyl ether
  3. dry with materialthe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by flash chromatography (silica gel; hexane/acetone 4:1)

出典と根拠

ORDレコード
ord-ca876f72bec145438615ac45933ab059
出典データセット
uspto-grants-2013_05
特許番号
US08450519B2

反応ノート

読み込み中…