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Triethylamine → 3-(4-Benzyloxy-phenyl)-2(S)-[2(S)-(4-tert-butyl-benzenesulfonylamino)-4-methyl-pentanoylamino]-propionic acid tert-butyl ester

HRID 2230317
ノート
印刷プレビュー

反応式

HRID 2230317 の反応式
[C:1]([O:5][C:6](=[O:32])[CH:7]([NH:23][C:24](=[O:31])[CH:25]([NH2:30])[CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:40]([C:44]1[CH:49]=[CH:48][C:47]([S:50](Cl)(=[O:52])=[O:51])=[CH:46][CH:45]=1)([CH3:43])([CH3:42])[CH3:41].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:32])[C@@H:7]([NH:23][C:24](=[O:31])[C@@H:25]([NH:30][S:50]([C:47]1[CH:48]=[CH:49][C:44]([C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:45][CH:46]=1)(=[O:52])=[O:51])[CH2:26][CH:27]([CH3:28])[CH3:29])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)([CH3:3])([CH3:2])[CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8471TriethylamineHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 540817292-(2-Amino-4-methyl-pentanoylamino)-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester

生成物 1

HCID 700600743-(4-Benzyloxy-phenyl)-2(S)-[2(S)-(4-tert-butyl-benzenesulfonylamino)-4-methyl-pentanoylamino]-propionic acid tert-butyl ester
収率 70%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A solution of the product from Example AI ([S-(R*,R*)]-2-{2-amino-4-methyl-pentanoylamino}-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester) (0.20 g, 0.45 mmol) and triethylamine (0.13 mL, 0.90 mmol) in 5 mL of CHCl3 was cooled to 0° C. and treated with 4-tert-butylphenylsulfonyl chloride (0.10 g, 0.45 mmol). The reaction mixture was warmed to room temperature and treated with saturated aqueous NaHCO3. The organic phase was separated from the aqueous phase. The aqueous phase was extracted with additional CHCl3, and the combined organic extracts were dried MgSO4, filtered, and concentrated. The residue was purified by chromatography (silica gel, 1:1 heptane/ethyl acetate). The chromatography product was crystallized from hot heptane/ethyl acetate to give the title compound as a white solid 0.20 g 70%), mp=142-143° C.

後処理

  1. customwas cooled to 0° C.
  2. customThe organic phase was separated from the aqueous phase
  3. extractionThe aqueous phase was extracted with additional CHCl3
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (silica gel, 1:1 heptane/ethyl acetate)
  7. customThe chromatography product was crystallized from hot heptane/ethyl acetate

出典と根拠

ORDレコード
ord-67168a69dbc34e30b7b758740b759fc5
出典データセット
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06423689B1

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート