Thionyl Chloride → 2-(R)-benzyloxycarbonylamino-3-(7-chloro-4-chloromethyl-1H-indazol-5-yl)propionic acid methyl ester

HRID 1985443ノート

反応式

HRID 1985443 の反応式
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7](=[O:33])[C@H:8]([NH:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[CH2:9][C:10]1[C:11]([CH2:20]O)=[C:12]2[C:16](=[C:17]([Cl:19])[CH:18]=1)[NH:15][N:14]=[CH:13]2>ClCCl>[CH3:5][O:6][C:7](=[O:33])[C@H:8]([NH:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[CH2:9][C:10]1[C:11]([CH2:20][Cl:3])=[C:12]2[C:16](=[C:17]([Cl:19])[CH:18]=1)[NH:15][N:14]=[CH:13]2

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 597319282-(R)-Benzyloxycarbonylamino-3-(7-chloro-4-hydroxymethyl-1H-indazol-5-yl)-propionic acid methyl ester

生成物 1

HCID 597318592-(R)-benzyloxycarbonylamino-3-(7-chloro-4-chloromethyl-1H-indazol-5-yl)propionic acid methyl ester収率 86%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Thionyl chloride (2 mL) was added to a solution of 2-(R)-benzyloxycarbonylamino-3-(7-chloro-4-hydroxymethyl-1H-indazol-5-yl)-propionic acid methyl ester (245 mg, 0.59 mmol) in dichloromethane (3 mL). Mixture was stirred at room temperature for 1.5 hours. Mixture was concentrated. Residue was dissolved in dichloromethane (15 mL) then washed with saturated aqueous sodium bicarbonate (2×10 mL). Organic was dried (magnesium sulfate), filtered and concentrated. Title compound was obtained as an orange solid in 86% yield. Material was carried forward without further purification. 1H NMR (300 MHz, CDCl3): δ=8.19 (s, 1H), 7.32 (m, 5H), 7.16 (s, 1H), 5.49 (d, J=7.3, 2H), 5.07 (d, J=4.4, 2H), 4.85 (s, 2H), 4.68 (d, J=7.0, 1H), 3.72 (s, 3H), 3.27 (m, 2H). MS m/e (M+H)+=436.1.

後処理

  1. concentrationMixture was concentrated
  2. dissolutionResidue was dissolved in dichloromethane (15 mL)
  3. washthen washed with saturated aqueous sodium bicarbonate (2×10 mL)
  4. dry with materialOrganic was dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-3e34a02cc1e74664a81e4df22a8578d4
出典データセット
uspto-grants-2009_06
特許番号
US07544680B2

反応ノート

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