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Trityl chloride → HCID 72698639、化合物

HRID 1482231
ノート
印刷プレビュー

反応式

HRID 1482231 の反応式
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:23][C:24]3[NH:28][N:27]=[N:26][N:25]=3)[C:20]([OH:22])=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)C(C)C)(C)C.[C:38](Cl)([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>O1CCCC1>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:23][C:24]3[N:28]([C:38]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:51]4[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=4)[C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)[N:27]=[N:26][N:25]=3)[C:20]([OH:22])=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:23][C:24]3[N:25]=[N:26][N:27]([C:38]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:51]4[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=4)[C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)[N:28]=3)[C:20]([OH:22])=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6456Trityl chlorideHCID 81531DiisopropylethylamineHCID 71744314(2S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(1H-1,2,3,4-tetrazol-5-yl)propanoic acidHCID 178523879HCID 178523879、化合物

生成物 2

HCID 72698639HCID 72698639、化合物HCID 117735885
HCID 117735885、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

(2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(1H-tetrazol-5-yl)propanoic acid and (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(2H-tetrazol-5-yl)propanoic acid (Compound SP410, Fmoc-Ala(5-Tet)-OH) (900 mg, 2.37 mmol) were dissolved in tetrahydrofuran (2.7 ml), N,N-diisopropylethylamine (0.36 mL, 2.61 mmol) was added and the mixture was stirred for 5 minutes. A solution of trityl chloride (628 mg, 2.25 mmol) dissolved in tetrahydrofuran (0.6 ml) was added to the aforementioned reaction solution, and the mixture was stirred for 90 minutes. The reaction solution was filtered, and the collected reaction solution was concentrated under reduced pressure, and the residue was purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol) to afford (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(1-trityltetrazol-5-yl)propanoic acid and (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(2-trityltetrazol-5-yl)propanoic acid (Compound SP409, Fmoc-Ala(5-Tet(Trt))-C)H) (644 mg, 44%).

後処理

  1. additionwas added to the aforementioned reaction solution
  2. stirringthe mixture was stirred for 90 minutes
  3. filtrationThe reaction solution was filtered
  4. customthe collected reaction solution
  5. concentrationwas concentrated under reduced pressure
  6. customthe residue was purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol)

出典と根拠

ORDレコード
ord-68109aa1c2c4496594605ab2a37b8a71
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09409952B2

反応ノート

読み込み中…

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