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Ethanol → benzyl ((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-hydroxy-1-isopropylbutyl)carbamate

HRID 906957
ノート
印刷プレビュー

反応式

HRID 906957 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH:28]([CH3:30])[CH3:29])[CH:13]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:14][C:15](OCC)=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].C(O)C>C1COCC1.C(OCC)(=O)C>[Si:21]([O:20][CH:13]([CH2:14][CH2:15][OH:16])[C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:28]([CH3:30])[CH3:29])([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 67390315ethyl (4S)-4-{[(benzyloxy)carbonyl]amino}-3-{[tert-butyl(dimethyl)silyl]oxy}-5-methylhexanoate

生成物 1

HCID 86640708benzyl ((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-hydroxy-1-isopropylbutyl)carbamate収率 93.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

Under an argon atmosphere, to a suspension (303 mL) of ethyl (4S)-4-{[(benzyloxy)carbonyl]amino}-3-{[tert-butyl(dimethyl)silyl]oxy}-5-methylhexanoate (17.7 g), calcium chloride (6.73 g) and sodium borohydride (4.58 g) in dehydrated THF was added with stirring under ice-cooling dehydrated ethanol (152 mL), and the mixture was gradually warmed to room temperature and stirred for 15 hr. The reaction mixture was slowly poured into a mixture of ethyl acetate and ice water (containing 1 mol/L hydrochloric acid, 122 mL) and the mixture was partitioned. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=19/1→1/1) to give benzyl ((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-hydroxy-1-isopropylbutyl)carbamate as colorless oil (yield: 14.9 g).

後処理

  1. stirringstirred for 15 hr
  2. customthe mixture was partitioned
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=19/1→1/1)

出典と根拠

ORDレコード
ord-2c36faa00f764cba848ee15c192bd6ec
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08013008B2

反応ノート

読み込み中…

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