Triphenylphosphine → Methyl 3-(4-{[4-(chloromethyl)benzyl][(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

HRID 507909ノート

反応式

HRID 507909 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:16][CH:15]=1)(=[O:12])=[O:11])([O-:3])=[O:2].[Cl:26][CH2:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]O)=[CH:30][CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[Cl:26][CH2:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][N:13]([S:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])[C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:16][CH:15]=2)=[CH:30][CH:29]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5107660[4-(Chloromethyl)phenyl]methanolHCID 23157467Methyl 3-(4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

生成物 1

HCID 23157281Methyl 3-(4-{[4-(chloromethyl)benzyl][(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate収率 95.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of methyl 3-(4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (2.78 g, 7.63 mmol), 4-chloromethylbenzyl alcohol (1.21 g, 7.70 mmol) and triphenylphosphine (3.93 g, 15.4 mmol) in toluene (150 mL) was stirred under ice-cooling. Diethyl azodicarboxylate (40% toluene solution, 6.98 μmL, 15.4 mmol) was added, and the mixture was allowed to warm to room temperature and stirred for 72 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (20%-60% ethyl acetate/hexane). Hexane-ethyl acetate was added to the obtained residue, and the resultant insoluble material was filtered off. The filtrate was concentrated to give the title compound (3.65 g, yield 95%) as a red oil.

後処理

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (20%-60% ethyl acetate/hexane)
  4. additionHexane-ethyl acetate was added to the obtained residue
  5. filtrationthe resultant insoluble material was filtered off
  6. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-bec1acceaea242e2aa009d7f2137bcb3
出典データセット
uspto-grants-2010_08
特許番号
US07786165B2

反応ノート

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