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 1798288ノート

反応式

HRID 1798288 の反応式
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]

参加物

6

反応物 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

生成物 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 acid収率 40%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-95be7d71fe7b4962a73e4a3975902f00
出典データセット
uspto-grants-2013_01
特許番号
US08343944B2

反応ノート

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