Diethylene Glycol Monomethyl Ether → N-(2-{[3-Chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-succinamic acid 2-(2-methoxy-ethoxy)ethyl ester

HRID 1797316

反応式

HRID 1797316 の反応式
CCOC(/N=N/C(OCC)=O)=O.[Cl:13][C:14]1[CH:15]=[C:16]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[NH:36][C:37](=[O:43])[CH2:38][CH2:39][C:40]([OH:42])=[O:41])[CH:17]=[CH:18][C:19]=1[C:20](=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:63][O:64][CH2:65][CH2:66][O:67][CH2:68][CH2:69]O>C1(C)C=CC=CC=1.CCOC(C)=O.O>[CH3:63][O:64][CH2:65][CH2:66][O:67][CH2:68][CH2:69][O:41][C:40](=[O:42])[CH2:39][CH2:38][C:37]([NH:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[NH:29][C:16]1[CH:17]=[CH:18][C:19]([C:20](=[O:28])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])=[C:14]([Cl:13])[CH:15]=1)=[O:43]

参加物

8

反応物 4

HCID 8134Diethylene Glycol Monomethyl EtherHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 9845903N-[2-[3-Chloro-4-(2-methylbenzoyl)-phenylamino]phenyl]-succinamic Acid

生成物 1

HCID 69663252N-(2-{[3-Chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-succinamic acid 2-(2-methoxy-ethoxy)ethyl ester

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of diethylazodicarboxylate (40% in toluene, 229 μL, 0.5 mmol) was slowly added to a mixture of N-(2-{[3-chloro-4-(2-methylbenzoyl)phenyl]amino}phenyl)-succinamic acid (200 mg, 0.46 mmol) (disclosed in WO 01/05746), triphenylphosphine (132 mg, 0.50 mmol), and 2-(2-methoxyethoxy)ethanol (55 mg, 0.46 mmol) in dry toluene (2.5 ml). The reaction mixture was stirred for 48 h and then poured into a mixture of water and EtOAc. The aqueous phase was extracted with more EtOAc (×2). The combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc as the eluent to afford the title compound as a yellow oil.

後処理

  1. extractionThe aqueous phase was extracted with more EtOAc (×2)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-3b3b7a0bd78c440686b1c6c5346051a3
出典データセット
uspto-grants-2006_04
特許番号
US07034015B2

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