Ethyl Acetate → HCID 66847432、化合物

HRID 58384

反応式

HRID 58384 の反応式
Cl.[CH3:2][O:3][C:4]([C@H:6]1[NH:22][C:21](=[O:23])[C@H:20]([CH:24]([CH3:26])[CH3:25])[NH:19][C:18](=[O:27])[C@@H:17]([NH2:28])[CH2:16][C:15]2=[CH:29][CH:30]=[C:12]([CH:13]=[CH:14]2)[O:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].[CH3:31][S:32](Cl)(=[O:34])=[O:33].CCN(C(C)C)C(C)C.CCOC(C)=O>CN(C=O)C>[CH3:2][O:3][C:4]([C@H:6]1[NH:22][C:21](=[O:23])[C@H:20]([CH:24]([CH3:26])[CH3:25])[NH:19][C:18](=[O:27])[C@@H:17]([NH:28][S:32]([CH3:31])(=[O:34])=[O:33])[CH2:16][C:15]2=[CH:29][CH:30]=[C:12]([CH:13]=[CH:14]2)[O:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86650244(7S,10S,13S)-13-Amino-10-isopropyl-9,12-dioxo-2-oxa-8,11-diaza-bicyclo[13.2.2]nonadeca-1-(18),15(19),16-triene-7-carboxylic acid methyl ester hydrogen chloride salt

生成物 1

HCID 66847432HCID 66847432、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Amine 47 (200 mg) was dissolved in anhydrous DMF (5 mL). Methane-sulfonyl chloride (39 μL) and DIPEA (0.175 mL) were added and the reaction mixture was stirred at rt for 18 h before being partitioned between chloroform and 1M hydrochloric acid. The aqueous phase was extracted three more times with chloroform and the combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. Purification was achieved using flash chromatography, eluting with a gradient of 1/1 EtOAc/(50/70) petroleum ether to EtOAc to yield a light brown solid, 40 mg, 17%. Rf=0.12 (1/1 EtOAc/(50/70) petroleum ether).

後処理

  1. custombefore being partitioned between chloroform and 1M hydrochloric acid
  2. extractionThe aqueous phase was extracted three more times with chloroform
  3. dry with materialthe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification
  7. washeluting with a gradient of 1/1 EtOAc/(50/70) petroleum ether to EtOAc
  8. customto yield a light brown solid, 40 mg, 17%

出典と根拠

ORDレコード
ord-575659e4f17d478492d17ddc7a65ed3b
出典データセット
uspto-grants-2016_09
特許番号
US09434762B2

関連ノート

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