Water → ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-(tert-butyldimethylsilyloxy)hexanoate

HRID 1173619ノート

反応式

HRID 1173619 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:21][CH3:22])[CH:13]([OH:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.FC(F)(F)S(O)(=O)=O.[C:39]([SiH:43]([CH3:45])[CH3:44])([CH3:42])([CH3:41])[CH3:40].O>O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:21][CH3:22])[CH:13]([O:20][Si:43]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:45])[CH3:44])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 79372,6-LutidineHCID 67105208ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-hydroxyhexanoateHCID 131728534Tert-butyldimethylsilane trifluoromethanesulfonate

生成物 1

HCID 67105077ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-(tert-butyldimethylsilyloxy)hexanoate収率 74%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-hydroxyhexanoate (63.2 g) and 2,6-lutidine (47.6 mL) in tetrahydrofuran (800 mL) was added tert-butyldimethylsilane trifluoromethanesulfonate (70 mL) under ice-cooling and, after warming to room temperature, and the mixture was stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/0→1/1) to give ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-(tert-butyldimethylsilyloxy)hexanoate as a colorless oil (yield: 64.0 g, 74%).

後処理

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/0→1/1)

出典と根拠

ORDレコード
ord-63bc6586e75f44e591cc8d7ff39cbff4
出典データセット
uspto-grants-2010_11
特許番号
US07834051B2

反応ノート

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