Benzenesulfonyl chloride → HCID 178472453、化合物

HRID 1613491ノート

反応式

HRID 1613491 の反応式
[C:1]([O:5][C:6](=[O:29])[CH:7]([NH2:28])[CH2:8][C:9]1([C:14](=[O:27])[NH:15][C@H:16]2[CH2:21][CH2:20][C@@H:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:37]1([S:43](Cl)(=[O:45])=[O:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>ClCCl>[C:1]([O:5][C:6](=[O:29])[CH:7]([NH:28][S:43]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(=[O:45])=[O:44])[CH2:8][C:9]1([C:14](=[O:27])[NH:15][C@H:16]2[CH2:17][CH2:18][C@@H:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:20][CH2:21]2)[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:2])([CH3:3])[CH3:4]

参加物

5

反応物 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 178472452HCID 178472452、化合物

生成物 1

HCID 178472453HCID 178472453、化合物収率 74%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

2-Amino-3-{1-[(cis-4-ethoxycarbonyl-cyclohexyl)carbamoyl]-cyclopentyl}propanoic acid t-butyl ester (0.605 g, 1.48 mmole) was dissolved in dry dichloromethane (25 ml) and treated at 0° C. with triethylamine (0.45 g, 4.4 mmole) and benzene sulphonyl chloride (0.24 ml, 1.84 mmole). After stirring for 16 hours at room temperature under nitrogen the dichloromethane was removed under vacuum, the residue taken up in diethyl ether (25 ml), washed with dilute hydrochloric acid, dilute sodium hydrogen carbonate and water, dried (Na2SO4) and the solvent evaporated under vacuum to give the crude product. Purification by column chromatography on silica, eluting with diethyl etherdichloromethane mixtures, gave pure title compound as a white foam (0.60 g, 74%). Found: C,61.38; H,7.85; N,5.06. C28H42N2O7S requires C,61.06; H,7.69; N,5.09%.

後処理

  1. customwas removed under vacuum
  2. washwashed with dilute hydrochloric acid, dilute sodium hydrogen carbonate and water
  3. dry with materialdried (Na2SO4)
  4. customthe solvent evaporated under vacuum
  5. customto give the crude product
  6. customPurification by column chromatography on silica
  7. washeluting with diethyl etherdichloromethane mixtures

出典と根拠

ORDレコード
ord-cd56313061f840d891626cee359576ed
出典データセット
uspto-grants-1993_03
特許番号
US05192800

反応ノート

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