Water → Dimethylcarbamic acid 3-{3-((tert-butoxycarbonyl)aminosulfonyl)aminobenzyl}-6-chloro-4-fluoromethyl-2-oxo-2H-1-benzopyran-7-yl ester

HRID 599834ノート

反応式

HRID 599834 の反応式
C(N(CC)CC)C.[C:8]([O:12][C:13]([N-:15][S:16](N1C=CC(=[N+](C)C)C=C1)(=[O:18])=[O:17])=[O:14])([CH3:11])([CH3:10])[CH3:9].[NH2:28][C:29]1[CH:30]=[C:31]([CH:53]=[CH:54][CH:55]=1)[CH2:32][C:33]1[C:34](=[O:52])[O:35][C:36]2[CH:44]=[C:43]([O:45][C:46](=[O:50])[N:47]([CH3:49])[CH3:48])[C:42]([Cl:51])=[CH:41][C:37]=2[C:38]=1[CH2:39][F:40].O>ClCCl>[C:8]([O:12][C:13]([NH:15][S:16]([NH:28][C:29]1[CH:30]=[C:31]([CH:53]=[CH:54][CH:55]=1)[CH2:32][C:33]1[C:34](=[O:52])[O:35][C:36]2[CH:44]=[C:43]([O:45][C:46](=[O:50])[N:47]([CH3:49])[CH3:48])[C:42]([Cl:51])=[CH:41][C:37]=2[C:38]=1[CH2:39][F:40])(=[O:18])=[O:17])=[O:14])([CH3:11])([CH3:9])[CH3:10]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 59139328dimethylcarbamic acid 3-(3-aminobenzyl)-6-chloro-4-fluoromethyl-2-oxo-2H-1-benzopyran-7-yl esterHCID 178482962HCID 178482962、化合物

生成物 1

HCID 59139501Dimethylcarbamic acid 3-{3-((tert-butoxycarbonyl)aminosulfonyl)aminobenzyl}-6-chloro-4-fluoromethyl-2-oxo-2H-1-benzopyran-7-yl ester収率 63%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Triethylamine (34 μL, 0.25 mmol) and N-(tert-butoxycarbonyl)-N-{4-(dimethylazaniumylidene)-1,4-dihydropyridin-1-ylsulfonyl}azanide (49 mg, 0.16 mmol) were added in series to a solution of dimethylcarbamic acid 3-(3-aminobenzyl)-6-chloro-4-fluoromethyl-2-oxo-2H-1-benzopyran-7-yl ester (compound 1h-1-3F) (33 mg, 0.082 mmol) in anhydrous dichloromethane (1.0 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was then poured into water and extracted with ethyl acetate. The organic extract was washed with saturated saline and dried over magnesium sulfate. A crude solid was then obtained by vacuum concentration, and purified by preparative TLC (ethyl acetate:hexane=1:2) to yield the title compound (30 mg, 63%) as a white powder.

後処理

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with saturated saline
  4. dry with materialdried over magnesium sulfate
  5. customA crude solid was then obtained by vacuum concentration
  6. custompurified by preparative TLC (ethyl acetate:hexane=1:2)

出典と根拠

ORDレコード
ord-62cf9484c72d4c61bde37eccf51d8d2c
出典データセット
uspto-grants-2011_03
特許番号
US07897792B2

反応ノート

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