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Triethylamine → (S)-3-[2-benzyloxy-4-(4-chloro-butanoylamino)-benzenesulfonylamino]-4,4-diethoxy-butyric acid tert-butyl ester

HRID 1814385
ノート
印刷プレビュー

反応式

HRID 1814385 の反応式
[C:1]([O:5][C:6](=[O:35])[CH2:7][C@H:8]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][C:21]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:19])=[O:18])[CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:43][CH2:44][CH2:45][CH2:46][C:47](Cl)=[O:48]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:35])[CH2:7][C@H:8]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:47](=[O:48])[CH2:46][CH2:45][CH2:44][Cl:43])=[CH:22][C:21]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:19])=[O:18])[CH:9]([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15])([CH3:3])([CH3:4])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 69692490(S)-3-(4-amino-2-benzyloxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester

生成物 1

HCID 69692699(S)-3-[2-benzyloxy-4-(4-chloro-butanoylamino)-benzenesulfonylamino]-4,4-diethoxy-butyric acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

反応条件

温度
0 °C

実験手順

To a solution of (S)-3-(4-amino-2-benzyloxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester from Route J step 7 (0.958 g, 1.88 mmol), in anhydrous methylene chloride (20 mL) at 0° C. was added triethylamine (1.32 mL, 9.42 mmol) followed by 4-chlorobutyryl chloride (0.32 ml, 2.83 mmol) dropwise. The reaction was allowed to stir at 0° C. for 1 h and then allowed to slowly warm to room temperature overnight. The methylene chloride was evaporated and the reaction mixture was dissolved in ethyl acetate and water. The organic layer was collected and washed with 10% sulfuric acid, brine, dried over magnesium sulfate, and concentrated to yield (S)-3-[2-benzyloxy-4-(4-chloro-butanoylamino)-benzenesulfonylamino]-4,4-diethoxy-butyric acid tert-butyl ester (1.32 g) as a crude brown oil. MS (APCI) m/z 611.3 (M−1).

後処理

  1. temperatureto slowly warm to room temperature overnight
  2. customThe methylene chloride was evaporated
  3. dissolutionthe reaction mixture was dissolved in ethyl acetate
  4. customThe organic layer was collected
  5. washwashed with 10% sulfuric acid, brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-401ea6ebada64f00bbd1afe271130566
出典データセット
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06875765B2

反応ノート

読み込み中…

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