Hydrochloric Acid → [6-(5-tert-Butoxycarbonylamino-thiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid

HRID 1798288노트

반응식

HRID 1798288 반응식
C([O:3][C:4](=[O:31])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[S:19][C:20]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:21][N:22]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[Li+].[OH-].Cl>C1COCC1.O>[C:27]([O:26][C:24]([NH:23][C:20]1[S:19][C:18]([O:17][C:13]2[CH:14]=[C:15]([CH3:16])[C:7]3[CH:6]([CH2:5][C:4]([OH:31])=[O:3])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)=[N:22][CH:21]=1)=[O:25])([CH3:30])([CH3:29])[CH3:28]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292561[6-(5-tert-Butoxycarbonylamino-thiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester

생성물 1

HCID 58292843[6-(5-tert-Butoxycarbonylamino-thiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid수율 40%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of [6-(5-tert-butoxycarbonylamino-thiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (270 mg, 0.6 mmol) in THF (7 mL) was added LiOH (76 mg, 1.8 mmol) in water (3.5 mL). The mixture was stirred at room temperature for 3 h and acidified by 1N HCl to pH 3. The mixture was extracted by ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated. The residue was purified by HPLC affording the title compound (100 mg, 40%) as a white solid. 1H NMR (CD3OD) δ 7.29 (s, 1H), 7.19 (s, 1H), 6.75 (s, 1H), 5.69 (dd, 1H), 3.19 (m, 1H), 2.40 (s, 3H), 2.35 (m, 1H), 1.52 (s, 9H). MS found: (M+H)+=421.20.

후처리

  1. extractionThe mixture was extracted by ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by HPLC

출처 및 근거

ORD 기록
ord-95be7d71fe7b4962a73e4a3975902f00
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343944B2

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