Ethanol → HCID 178464723, 화합물

HRID 1036404

반응식

HRID 1036404 반응식
[CH3:1][C@@:2]1([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][C@H:19]4[CH2:24][CH2:23][C@@H:22]([CH3:25])[CH2:21][CH2:20]4)[CH:14]=3)[CH:9]=2)[CH2:6][O:5]C(=O)[NH:3]1.C(O)C.O.[OH-].[Li+]>O>[NH2:3][C@@:2]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][C@H:19]3[CH2:20][CH2:21][C@@H:22]([CH3:25])[CH2:23][CH2:24]3)[CH:14]=2)[CH:9]=1)([CH3:1])[CH2:6][OH:5]

참가 물질

5

반응물 3

HCID 702EthanolHCID 168937Lithium hydroxide, monohydrateHCID 178421574HCID 178421574, 화합물

생성물 1

HCID 178464723HCID 178464723, 화합물수율 6%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

To a solution of (R)-4-Methyl-4-[6-(cis4-methyl-cyclohexyloxy)-naphthalen-2-yl]-oxazolidin-2-one (0.4420 g, 0.001302 mol) in ethanol (5.00 mL, 0.0856 mol) in a capped 40 mL vial was added 4.2 M Lithium hydroxide, monohydrate in water (2.8 mL). The mixture was heated overnight at 80° C. TLC analysis showed the reaction was complete. The mixture was concentrated to dryness under vacuum. Methylene chloride (5 mL) and water (5 mL) were added and the layers were separated (2×). The organic layer was concentrated under vacuum and purified by HPLC to give 0.0233 g of the title compound (6% yield). MS: m/z=297.29 [M−NH2]+. 1H NMR (400 MHz, MeOD) δ 0.98 (d, J=6.02 Hz, 3H), 1.40-1.51 (m, 2H), 1.51-1.60 (m, 3H), 1.64-1.74 (m, 2H), 1.79 (s, 3H), 2.03-2.14 (m, 2H), 3.83 (d, J=11.55 Hz, 1H), 3.93 (d, J=11.55 Hz, 1H), 4.69-4.77 (m, 1H), 7.23 (dd, J=8.91, 2.38 Hz, 1H), 7.27 (d, J=2.51 Hz, 1H), 7.53 (dd, J=8.78, 2.01 Hz, 1H), 7.79-7.89 (m, 3H)

후처리

  1. concentrationThe mixture was concentrated to dryness under vacuum
  2. additionMethylene chloride (5 mL) and water (5 mL) were added
  3. customthe layers were separated (2×)
  4. concentrationThe organic layer was concentrated under vacuum
  5. custompurified by HPLC

출처 및 근거

ORD 기록
ord-e4605061053247c280ea13972fb55ad0
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546359B2

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