Lithium hydroxide, monohydrate → HCID 69656586, 화합물

HRID 7029노트

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HRID 7029 반응식
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

참가 물질

6

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 69656016HCID 69656016, 화합물

생성물 1

HCID 69656586HCID 69656586, 화합물수율 80%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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)−.

후처리

  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

출처 및 근거

ORD 기록
ord-92fc3ebc156c49bb94c274736e08c176
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084178B2

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