Lithium hydroxide, monohydrate → HCID 69656586、化合物

HRID 7029ノート

反応式

HRID 7029 の反応式
O.[OH-].[Li+].C[O:5][C:6]([C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[NH:14][S:15]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)(=[O:17])=[O:16])=[O:7]>C1COCC1.CO.O>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([S:15]([NH:14][C@H:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C@H:8]2[C:6]([OH:7])=[O:5])(=[O:16])=[O:17])=[CH:19][CH:20]=1

参加物

6

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 69656016HCID 69656016、化合物

生成物 1

HCID 69656586HCID 69656586、化合物収率 80%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Lithium hydroxide monohydrate (1.7 mmol) was added to a mixture of (1R,2S)-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid methyl ester in THF (8 mL), methanol (8mL) and water (8 mL). Reaction stirred at room temperature overnight. Organic solvents were removed from the mixture in vacuo. Remaining aqueous was washed with ether (2×15 mL). Aqueous layer was made acidic to litmus paper with 1 N hydrochloric acid. Mixture was extracted with ethyl acetate (2×20 mL). Combined extracts were washed with brine (1×10 mL) then dried (magnesium sulfate), filtered and concentrated in vacuo. The product (208 mg) was obtained as a white solid in 80% yield: 1H NMR (300 Mz, CDCl3) δ 7.70 (d, 2 H, J=8.8), 7.48 (d, 4 H, J=8.8), 6.20 (d, 1 H, J=9.5), 3.41 (m, 1 H), 2.81 (dd, 1 H, Jd=4.4, Jd=4.8), 2.03 (m, 1 H), 1.80 (m, 1 H), 1.62 (m, 1 H), 1.44 (m, 2 H), 1.25 (m, 2 H); MS m/e 316 (M−H)−.

後処理

  1. customReaction
  2. customOrganic solvents were removed from the mixture in vacuo
  3. washRemaining aqueous was washed with ether (2×15 mL)
  4. extractionMixture was extracted with ethyl acetate (2×20 mL)
  5. washCombined extracts were washed with brine (1×10 mL)
  6. dry with materialthen dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-92fc3ebc156c49bb94c274736e08c176
出典データセット
uspto-grants-2006_08
特許番号
US07084178B2

反応ノート

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