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Lithium Hydroxide → [6-(5-Carbamoyl-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid

HRID 1798239
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인쇄 미리보기

반응식

HRID 1798239 반응식
C([O:3][C:4](=[O:27])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[CH:23]=[N:22][C:21]([C:24](=[O:26])[NH2:25])=[CH:20][N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[Li+].[OH-]>C1COCC1.O>[C:24]([C:21]1[N:22]=[CH:23][C:18]([O:17][C:13]2[CH:14]=[C:15]([CH3:16])[C:7]3[CH:6]([CH2:5][C:4]([OH:27])=[O:3])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)=[N:19][CH:20]=1)(=[O:26])[NH2:25]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 58292848[6-(5-Carbamoyl-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester

생성물 1

HCID 58292723[6-(5-Carbamoyl-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid수율 52.7%

시약·촉매·용매 2

HCID 962Water용매HCID 8028
Tetrahydrofuran
용매

실험 절차

A solution of [6-(5-carbamoyl-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (77 mg, 0.21 mmol) in THF (4 mL) was treated with LiOH (35 mg, 0.84 mmol) in water (4 mL) at room temperature for 1 h. The reaction was concentrated to dryness. The residue was diluted with water and adjusted to pH 3. The mixture was purified by preparative HPLC to give the title compound (38 mg). 1H NMR (300 MHz, CD3OD) δ 8.76 (s, 1H), 8.46 (s, 1H), 7.29 (s, 1H), 7.16 (s, 1H), 5.73-5.69 (m, 1H), 3.33-3.18 (m, 1H), 2.42 (s, 3H), 2.38-2.33 (m, 1H). MS found: (M+H)+: 344.1.

후처리

  1. concentrationThe reaction was concentrated to dryness
  2. additionThe residue was diluted with water
  3. customThe mixture was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-35336613fa264b618be275b3df52b82e
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08343944B2

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