Lithium hydroxide, monohydrate → HCID 59497497, 화합물

HRID 1747352노트

반응식

HRID 1747352 반응식
C[O:2][C:3](=[O:35])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH2:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([O:26][Si](C(C)(C)C)(C)C)=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)[C:7]1=[O:34].O.[OH-].[Li+]>C1COCC1.O>[OH:26][C:22]1[CH:21]=[C:20]2[C:25](=[CH:24][CH:23]=1)[C:16]([CH2:15][N:8]1[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:6]([CH2:5][CH2:4][C:3]([OH:35])=[O:2])[C:7]1=[O:34])=[CH:17][CH:18]=[CH:19]2

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 59497299HCID 59497299, 화합물

생성물 1

HCID 59497497HCID 59497497, 화합물수율 10.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 3-{3-[6-(tert-Butyl-dimethyl-silanyloxy)-naphthalen-1-ylmethyl]-2-oxo-2,3-dihydro-benzimidazol-1-yl}-propionic acid methyl ester (200 mg, 0.41 mmol) in THF (7 ml) and water (1 ml) was added lithium hydroxide monohydrate (26 mg, 0.61 mmol) at ambient temperature. Upon complete consumption of the starting material the reaction was diluted with water, ethyl acetate and 6N HCl (adjusted to pH=2). The layers were separated and the aqueous phase was extracted once with ethyl acetate. The combined organics were dried (MgSO4), filtered and concentrated. The remaining residue was diluted with acetonitrile (3 ml) and allowed to stand over night. The resulting precipitated product was collected via filtration, washed with acetonitrile and dried on house vacuum to give 15 mg (10%) of the desired product. LCMS (ESMS): m/z 363.38 (M+H+).

후처리

  1. customUpon complete consumption of the starting material the reaction
  2. additionwas diluted with water, ethyl acetate and 6N HCl (adjusted to pH=2)
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted once with ethyl acetate
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. additionThe remaining residue was diluted with acetonitrile (3 ml)
  9. waitto stand over night
  10. customThe resulting precipitated product
  11. filtrationwas collected via filtration
  12. washwashed with acetonitrile
  13. customdried on house vacuum

출처 및 근거

ORD 기록
ord-79168486105a461290f9950fc966ecc6
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150556B2

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