Oxalyl chloride → (+/-)-3-(3-Cyclopentyloxy-4-methoxyphenyl)sulfanyl-7-phenylheptanohydroxamic acid

HRID 381387ノート

反応式

HRID 381387 の反応式
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([S:15][CH:16]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:17][C:18](O)=[O:19])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.C[Si](C)(C)[O:39][NH2:40]>CN(C)C=O.ClCCl>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([S:15][CH:16]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:17][C:18]([NH:40][OH:39])=[O:19])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 65578Oxalyl chlorideHCID 2734666O-(Trimethylsilyl)hydroxylamineHCID 18363145(+/-)-3-(3-Cyclopentyloxy-4-methoxyphenyl)sulfanyl-7-phenylheptanoic acid

生成物 1

HCID 18363141(+/-)-3-(3-Cyclopentyloxy-4-methoxyphenyl)sulfanyl-7-phenylheptanohydroxamic acid

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

A stirred solution of (±)-3-(3-cyclopentyloxy-4-methoxyphenyl)sulfanyl-7-phenylheptanoic acid (0.40 g, Example 4) in a mixture of dimethylformamide (0.07 ml) and dichloromethane (20 ml) was treated dropwise with a solution of oxalyl chloride in dichloromethane (1.17 ml, 2.0 M). After stirring at room temperature for a further 30 minutes the mixture was treated dropwise with O-(trimethylsilyl)hydroxylamine (0.57 ml). The resulting white suspension was stirred for 10 minutes then partitioned between hydrochloric acid (50 ml, 1N) and ethyl acetate (50 ml). The aqueous layer was extracted twice with ethyl acetate (50 ml). The combined organic phases were washed with water (50 ml), then with brine (50 ml), then dried over magnesium sulphate and then evaporated to give the title compound (0.26 g) as a white foam. NMR (CDCl3): δ1.60 (m,8H), 1.86 (m,6H), 2.35 (br d,2H), 2.60 (br t,2H), 3.30 (m,1H), 3.80 (s,3H), 3.73 (m,1H), 6.76 (d,1H), 6.95 (d,2H), 7.10-7.30 (m,5H). Mass spectrum (FAB): m/z 444 (M+H)+.

後処理

  1. stirringThe resulting white suspension was stirred for 10 minutes
  2. customthen partitioned between hydrochloric acid (50 ml, 1N) and ethyl acetate (50 ml)
  3. extractionThe aqueous layer was extracted twice with ethyl acetate (50 ml)
  4. washThe combined organic phases were washed with water (50 ml)
  5. dry with materialwith brine (50 ml), then dried over magnesium sulphate
  6. customevaporated

出典と根拠

ORDレコード
ord-7e91a487fd2445d2b2ee5edeacb13383
出典データセット
uspto-grants-2001_10
特許番号
US06306873B1

反応ノート

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