Water → Ethyl 2-(6-(5-amino-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

HRID 1798293ノート

反応式

HRID 1798293 の反応式
O.[CH2:2]([O:4][C:5](=[O:27])[CH2:6][CH:7]1[O:11][B:10]([OH:12])[C:9]2[CH:13]=[C:14]([O:18][C:19]3[S:20][C:21]([N+:24]([O-])=O)=[N:22][N:23]=3)[CH:15]=[C:16]([CH3:17])[C:8]1=2)[CH3:3]>Cl.C(O)C.[Fe]>[CH2:2]([O:4][C:5](=[O:27])[CH2:6][CH:7]1[O:11][B:10]([OH:12])[C:9]2[CH:13]=[C:14]([O:18][C:19]3[S:20][C:21]([NH2:24])=[N:22][N:23]=3)[CH:15]=[C:16]([CH3:17])[C:8]1=2)[CH3:3]

参加物

6

反応物 2

HCID 962WaterHCID 58292621Ethyl 2-(1-hydroxy-4-methyl-6-(5-nitro-1,3,4-thiadiazol-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

生成物 1

HCID 58292641Ethyl 2-(6-(5-amino-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate収率 108.9%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid触媒HCID 23925Iron触媒HCID 702Ethanol溶媒

反応条件

温度
85 °C

実験手順

Concentrated HCl (10 drops) and water (12 ml) were added to a mixture of [6-(5-nitro-[1,3,4]thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.65 g, 1.71 mmol) and iron powder (0.479 g; 8.55 mmol) in ethanol (30 mL) at room temperature. The resulting mixture was stirred at 85° C. for 1.5 hours, cooled to room temperature and filtered through a pad of celite. The filtrate was evaporated and the residue dissolved in EtOAc (300 mL), washed with brine, dried over Na2SO4 and concentrated to give [6-(5-amino-[1,3,4]thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.650 g, 100%) which was used without further purification. 1HNMR (400 MHz, DMSO-d6) δ 9.33 (s, 1H), 7.33 (d, J=12.4 Hz, 1H), 7.18 (d, J=16.8 Hz, 1H), 5.51 (d, J=6.0 Hz, 1H), 4.02 (q, J=7.2 Hz, 2H), 3.10 (d, J=14.4 Hz, 1H), 2.33-2.31 (m, 1H), 2.30 (s, 3H), 1.10 (t, J=7.6 Hz, 3H). MS (ESI) m/z=350 [M+H]+.

後処理

  1. temperaturecooled to room temperature
  2. filtrationfiltered through a pad of celite
  3. customThe filtrate was evaporated
  4. dissolutionthe residue dissolved in EtOAc (300 mL)
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-9bfbf87d5f784bf6a3c4fbcfb8796ab7
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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