Lithium hydroxide, monohydrate → HCID 42597522, 화합물

HRID 1664112

반응식

HRID 1664112 반응식
[C:1]([NH:4][C@@H:5]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:18]3[C:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=4[CH:30]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=1)[C:6]([O:8]C)=[O:7])(=[O:3])[CH3:2].O.[OH-].[Li+]>C1COCC1.O.O>[C:1]([NH:4][C@@H:5]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:18]3[C:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=4[CH:30]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 42597520Methyl (2S)-2-acetamido-3-(4-[9-phenanthrenyl]phenyl)propanoate

생성물 1

HCID 42597522HCID 42597522, 화합물수율 55%

시약·촉매·용매 2

HCID 962Water용매HCID 21881883Oxolane--water (1/1)용매

실험 절차

To a solution of 98 (124 mg, 0.31 mmol) in THF/water, 2:1 (9 mL) was added lithium hydroxide monohydrate (26 mg, 0.62 mmol) and the resulting suspension was allowed to stir for 16 h. The reaction mixture was diluted with water (30 mL) and the THF was removed by evaporation. The aqueous layer was washed with DCM (40 mL) to remove unreacted starting material. The aqueous phase was acidified with 10% HCl and the resulting precipitate was extracted with DCM (3×40 mL). The combined organics were dried and evaporated to yield the title compound (65 mg, 0.17 mmol, 55%) as a white solid. Mp 128-132° C. [α]D20 +36.8 (c. 0.1, EtOH). 1H NMR (CD3OD, 300 MHz): δ 8.71 (d, J=8.1 Hz, 1H, ArH4″); 8.66 (d, J=8.4 Hz, 1H, ArH3″); 7.79 (s, 1H, ArH1″); 7.76 (s, 1H, ArH10″); 7.51 (m, 5H, ArH7″, ArH6″, ArH5″, ArH2″ and ArH1″); 7.32 (m, 2H, Ar′H); 4.76 (dd, J=5.1, 9.0 Hz, 1H, H2); 3.29 (dd, J=4.8, 13.5 Hz, 1H, H3a); 3.03 (dd, J=8.7, 13.5 Hz, 1H, H3b); 1.95 (s, 3H, COCH3). Mass Spectrum (ES, +ve) m/z 384 (50%) [MH+]. HRMS calcd for C25H22NO3 384.1600, found 384.1628.

후처리

  1. customthe THF was removed by evaporation
  2. washThe aqueous layer was washed with DCM (40 mL)
  3. customto remove unreacted
  4. extractionthe resulting precipitate was extracted with DCM (3×40 mL)
  5. customThe combined organics were dried
  6. customevaporated

출처 및 근거

ORD 기록
ord-81e143deb3b541d39b28898d0bf91b8b
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039430B2

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