Azidotrimethylsilane → HCID 46179902、化合物

HRID 1425696ノート

反応式

HRID 1425696 の反応式
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8](=[O:16])[C@H:9]([NH:12][C:13](=[O:15])[CH3:14])[CH2:10][OH:11])=[CH:4][CH:3]=1.[Si]([N:23]=[N+:24]=[N-])(C)(C)C>CC#N>[N:1]([C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8](=[O:16])[C@H:9]([NH:12][C:13](=[O:15])[CH3:14])[CH2:10][OH:11])=[CH:17][CH:18]=1)=[N+:23]=[N-:24]

参加物

4

反応物 2

HCID 78378AzidotrimethylsilaneHCID 46179901HCID 46179901、化合物

生成物 1

HCID 46179902HCID 46179902、化合物収率 79.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a cooled (0° C.) CH3CN solution (70 mL) of (R)—N-(4-aminobenzyl)-2-acetamido-3-hydroxypropanamide (2.40 g, 9.56 mmol) maintained under Ar, t-BuONO (3.41 mL, 28.68 mmol) followed by TMSN3 (3.02 mL, 22.94 mmol) were slowly added. The resulting solution was allowed to stir at room temperature (16 h) under Ar. The solvent was removed in vacuo, and the product was purified by column chromatography (SiO2; 1/9 MeOH/CHCl3) to give 2.10 g (79%) of (R)—N-(4-azidobenzyl)-2-acetamido-3-hydroxypropanamide as a white solid: mp 161-163° C.; [α]26D +13.2° (c 1.0, MeOH); Rf=0.35 (1/9 MeOH/CHCl3); IR (nujol mull) 3268, 2924, 2128, 1649, 1553, 1459 cm−1; 1H NMR (DMSO-d6) δ 1.87 (s, CH3C(O)), 3.58 (t, J=5.7 Hz, CH2OH), 4.26-4.32 (m, CH2Ar and CH), 4.91 (t, J=5.7 Hz, OH), 7.03-7.08 (m, 2 ArH), 7.28-7.31 (m, 2 ArH), 7.94 (d, J=8.1 Hz, NHCH), 8.40 (t, J=6.0 Hz, NHCH2); 13C NMR (DMSO-d6) δ 22.7 (CH3C(O)), 41.5 (CH2Ph), 55.3 (CH), 61.7 (CH2OH), 118.9, 128.7, 136.5, 137.7 (C6H5), 169.4, 170.3 (2 C(O)); HRMS (ESI) 278.1249 [M+H+] (calcd. for C12H16N5O3 278.1253); Anal. (C12H15N5O3) Calcd.: C, 51.98%; H, 5.45%; N, 25.26%. Found: C, 51.93%; H, 5.47%; N, 24.98%.

後処理

  1. temperaturemaintained under Ar
  2. additionwere slowly added
  3. customThe solvent was removed in vacuo
  4. customthe product was purified by column chromatography (SiO2; 1/9 MeOH/CHCl3)

出典と根拠

ORDレコード
ord-f9cb24ffad004d199b122f3fbf516337
出典データセット
uspto-grants-2015_01
特許番号
US08933065B2

反応ノート

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