Triethylamine → 4-(4'methoxyphenyl)-benzenesulfonyl-S-trityl-L-cysteine amide

HRID 352401ノート

反応式

HRID 352401 の反応式
[C:1]([S:20][CH2:21][C@@H:22]([C:24]([NH2:26])=[O:25])[NH2:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:34][O:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[CH:47]=[CH:46][C:45]([S:48](Cl)(=[O:50])=[O:49])=[CH:44][CH:43]=2)=[CH:38][CH:37]=1>C(Cl)Cl>[CH3:34][O:35][C:36]1[CH:37]=[CH:38][C:39]([C:42]2[CH:47]=[CH:46][C:45]([S:48]([NH:23][C@H:22]([C:24]([NH2:26])=[O:25])[CH2:21][S:20][C:1]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)(=[O:50])=[O:49])=[CH:44][CH:43]=2)=[CH:40][CH:41]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 27947504'-Methoxybiphenyl-4-sulfonyl chlorideHCID 44432703(2R)-2-amino-3-((triphenylmethyl)sulfanyl)propanamide

生成物 1

HCID 1317244584-(4'methoxyphenyl)-benzenesulfonyl-S-trityl-L-cysteine amide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Part C: To a solution of 2.93 grams (8.1 mmol) of S-trityl-L-cysteine amide in 50 mL of dry methylene chloride was added 2 equivalents of triethylamine followed by 2.29 grams (8.1 mmol) of 4-(4′-methoxyphenyl)phenylsulfonyl chloride. The solution was stirred at room temperature for one hour, then concentrated on a rotory evaporator. The resulting slurry was partitioned between ethyl acetate and water. The organics were washed with 5% potassium hydrogen sulfate, saturated sodium bicarbonate, and brine, dried over sodium sulfate, filtered and concentrated to give 4.2 grams of crude product. The crude material was purified by silica gel chromatography using 1:1 ethyl acetate:hexane as the eluent to yield 3.36 grams of pure N-(4-(4′methoxyphenyl)-benzenesulfonyl-S-trityl-L-cysteine amide as a white solid.

後処理

  1. concentrationconcentrated on a rotory evaporator
  2. customThe resulting slurry was partitioned between ethyl acetate and water
  3. washThe organics were washed with 5% potassium hydrogen sulfate, saturated sodium bicarbonate, and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give 4.2 grams of crude product
  8. customThe crude material was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-8bf0c0ec5cae4a4eafeb2c9833d6f2bf
出典データセット
uspto-grants-2004_06
特許番号
US06747027B1

反応ノート

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