Sodium Acetate → [(3R*,4S*,5S*)-5-(3-Fluoro-4-nitro-benzyl)-4-hydroxy-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-3-yl]-carbamic acid tert-butyl ester

HRID 420267ノート

反応式

HRID 420267 の反応式
[C:1]([O:5][C:6](=[O:26])[NH:7][C@@H:8]1[C@H:13]([OH:14])[C@H:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([F:25])[CH:17]=2)[CH2:11]S[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].O[O:28][S:29]([O-:31])=O.[K+].CC([O-])=O.[Na+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[C:1]([O:5][C:6](=[O:26])[NH:7][C@@H:8]1[C@@H:13]([OH:14])[C@H:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([F:25])[CH:17]=2)[CH2:11][S:29](=[O:31])(=[O:28])[CH2:9]1)([CH3:3])([CH3:4])[CH3:2]

参加物

7

反応物 4

HCID 517045Sodium AcetateHCID 656671Sodium PyrosulfiteHCID 23707502Potassium hydroxy sulfiteHCID 68553360[(3R*,4R*,5S*)-5-(3-Fluoro-4-nitro-benzyl)-4-hydroxy-tetrahydro-thiopyran-3-yl]-carbamic acid tert-butyl ester

生成物 1

HCID 131729359[(3R*,4S*,5S*)-5-(3-Fluoro-4-nitro-benzyl)-4-hydroxy-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-3-yl]-carbamic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

To a solution of [(3R*,4R*,5S*)-5-(3-fluoro-4-nitro-benzyl)-4-hydroxy-tetrahydro-thiopyran-3-yl]-carbamic acid tert-butyl ester (0.78 g, 2.0 mmol) in THF (15 mL) was added water (15 mL) and oxone (2.62 g, 4.2 mmol) and the reaction mixture was stirred for 2 h at 25° C. The excess oxone was destroyed after addition of 2 equivalents of NaOAc with sodium meta-bisulfite and the product was extracted with EtOAc. Combined extracts were washed with brine, dried over MgSO4 and evaporated. The title compound was obtained as a light yellow solid suitable for use in the next step: TLC (toluene-EtOAc 1:1) Rf=0.18; HPLC RtA=1.67 min; ESIMS [M+NH4]+=436; 1H NMR (600 MHz, DMSO-d6): δ 8.11 (t, 1H), 7.41 (d, 1H), 7.27 (d, 1H), 6.71 (d, 1H), 5.22 (d, 1H), 3.72 (m, 1H), 3.0-3.2 (m, 5H), 2.82 (s, 1H), 2.71 (dd, 1H), 2.17 (dd, 1H), 1.38 (s, 9H).

後処理

  1. customThe excess oxone was destroyed
  2. extractionthe product was extracted with EtOAc
  3. washCombined extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated

出典と根拠

ORDレコード
ord-a2d887294b414eca82c8a64a64251e82
出典データセット
uspto-grants-2012_01
特許番号
US08093406B2

反応ノート

読み込み中…