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

HRID 1985443노트

반응식

HRID 1985443 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3e34a02cc1e74664a81e4df22a8578d4
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544680B2

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