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Diisopropylethylamine → Boc-Ser(Bn)-Val-Val-Gly-Gly-OMe

HRID 2370905
ノート
印刷プレビュー

反応式

HRID 2370905 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:19]([NH:21][C@H:22]([C:26]([NH:28][C@H:29]([C:33]([OH:35])=O)[CH:30]([CH3:32])[CH3:31])=[O:27])[CH:23]([CH3:25])[CH3:24])=[O:20])[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.[CH3:43][O:44][C:45](=[O:52])[CH2:46][NH:47][C:48](=[O:51])[CH2:49][NH2:50].C(N(CC)C(C)C)(C)C.C1C=C2N=NN(O)C2=CC=1.O.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH3:43][O:44][C:45](=[O:52])[CH2:46][NH:47][C:48](=[O:51])[CH2:49][NH:50][C:33](=[O:35])[C@H:29]([CH:30]([CH3:32])[CH3:31])[NH:28][C:26](=[O:27])[C@H:22]([CH:23]([CH3:24])[CH3:25])[NH:21][C:19](=[O:20])[C@H:9]([CH2:10][O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]
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

7

反応物 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 86671345Glycyl glycine methyl ester trifluoroacetateHCID 86671355N-tert-butoxycarbonyl O-benzyl L-seryl L-valyl L-valine

生成物 1

HCID 86671365
Boc-Ser(Bn)-Val-Val-Gly-Gly-OMe
収率 78%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

N-tert-butoxycarbonyl O-benzyl L-seryl L-valine 17 (2.20 g, 4.46 mmol) and glycyl glycine methyl ester trifluoroacetate 21 (1.16 g, 4.44 mmol) were dissolved in CH2Cl2 (15 mL). N,N-diisopropylethyl amine (0.57 g, 4.4 mmol) and HOBt hydrate (0.68 g, 4.4 mmol) were added and the solution cooled to 0° C. EDC hydrochloride (0.94 g, 4.9 mmol) was added slowly together with 5 mL CH2Cl2. The reaction mixture was stirred for 1 h 30 min at 0° C. after which the icebath was removed. The mixture was stirred for an additional 23 hours before the volume was increased by addition of CH2Cl2 (20 mL). The solution was washed with 2 M aqueous H2SO4 (3×30 mL), 7.5% (w/w) aqueous K2CO3 (3×30 mL) and saturated brine (30 mL). The volume of the solution was increased, the solution dried with anhydrous MgSO4 and the solvent evaporated affording an off-white solid (2.14 g, 78%); δH (300 MHz; d6-DMSO) 8.25-8.20 (2H, m, NH(Gly1)/NH(Gly2)), 7.93 (1H, d, J 8, NH(Valx)), 7.70 (1H, d, J 9, NH(Valy)), 7.35-7.25 (5H, m, Ph), 7.06 (1H, d, J 8, NH(Ser(Bn))), 4.47 (2H, s, CH2Ph), 4.32-4.23 (2H, m, CαH(Ser(Bn))/CαH(Val)), 4.11 (1H, dd, J, CαH(Val)), 3.86 (2H, m, CαH2(Gly)), 3.75 (2H, d, J 6, CαHH(Gly)), 3.62 (3H, s, OCH3), 3.60-3.53 (2H, m, CH2), 2.01-1.88 (2H, m, CH(CH3)2), 1.38 (9H, s, (CH3)3), 0.85-0.78 (12H, m, CH3); δC (75 MHz; d6-DMSO) 171.1, 170.9, 170.1, 169.6, 169.1, 155.2, 138.1, 128.0, 127.4, 127.3, 78.2, 71.9, 69.8, 58.1, 57.2, 54.5, 51.6, 41.6, 40.5, 30.8, 30.1, 28.1, 19.1, 18.2, 17.8; m/z (ESI) 644.3268 ([M+Na]+; C30H47N5O9Na requires 644.3271)

後処理

  1. customwas removed
  2. stirringThe mixture was stirred for an additional 23 hours before the volume
  3. temperaturewas increased by addition of CH2Cl2 (20 mL)
  4. washThe solution was washed with 2 M aqueous H2SO4 (3×30 mL), 7.5% (w/w) aqueous K2CO3 (3×30 mL) and saturated brine (30 mL)
  5. temperatureThe volume of the solution was increased
  6. dry with materialthe solution dried with anhydrous MgSO4
  7. customthe solvent evaporated

出典と根拠

ORDレコード
ord-78a28cbc47bd4d8f8eb8486126099a5d
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08710008B2

反応ノート

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