2-Hydroxyphenyl hydrogen sulfate → HCID 69666265、化合物

HRID 722139ノート

反応式

HRID 722139 の反応式
[S:1]([O:5][C:6]1[C:7](=[CH:9][CH:10]=[CH:11][CH:12]=1)[OH:8])([OH:4])(=[O:3])=O.[F:13][C:14]1[C:15]2[CH2:16][CH:17]3[CH:26]([NH2:27])[CH:20]([CH2:21][C:22]=2[CH:23]=[CH:24][CH:25]=1)[CH2:19][CH2:18]3>C1COCC1.C(OCC)(=O)C>[OH:8][C:7]1[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=1[O:5][S:1](=[O:3])(=[O:4])[NH:27][CH:26]1[CH:20]2[CH2:19][CH2:18][CH:17]1[CH2:16][C:15]1[C:14]([F:13])=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:21]2

参加物

5

反応物 2

HCID 30838792-Hydroxyphenyl hydrogen sulfateHCID 21882818HCID 21882818、化合物

生成物 1

HCID 69666265HCID 69666265、化合物収率 51%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Catechol sulphate (332 mg, 1.93 mmol) was added to an ice-cooled solution of the amine from Step 4 (360 mg, 1.76 mmol) in THF (5 ml). The mixture was allowed to warm to room temperature, stirred for 18 hours, diluted with ethyl acetate and washed with ammonium chloride (aq) followed by brine. The organic phase was dried and evaporated to give a crude oil which was purified by column chromatography on silica gel eluting with 4:1 isohexane-ethyl acetate to give an orange oil 335 mg (51%). 1H NMR (CDCl3, 360 MHz) δ 7.27 (1H, m), 7.21 (1H, m), 7.05 (2H, m), 6.85–7.95 (3H, m), 6.32 (1H, br s), 5.40 (1H, br d, J=7.5 Hz), 4.02 (1H, q, J=6.4 Hz), 3.19–3.25 (1H, dd, J=16.7, 7.6 Hz), 3.04 (1H, d, J=16.3 Hz), 2.70 (1H, m), 2.50–2.61 (3H, m), 1.74 (2H, m), 1.21 (2H, m). m/z 376 (M−H)−

後処理

  1. washwashed with ammonium chloride (aq)
  2. customThe organic phase was dried
  3. customevaporated
  4. customto give a crude oil which
  5. customwas purified by column chromatography on silica gel eluting with 4:1 isohexane-ethyl acetate

出典と根拠

ORDレコード
ord-15e82746cdc04f2ab8f65519a7ca7f17
出典データセット
uspto-grants-2006_11
特許番号
US07138400B2

反応ノート

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