Trifluoroacetic acid → L-valyl L-valine methyl ester trifluoroacetate

HRID 588926ノート

反応式

HRID 588926 の反応式
[CH3:1][O:2][C:3](=[O:23])[C@H:4]([CH:20]([CH3:22])[CH3:21])[NH:5][C:6](=[O:19])[C@H:7]([CH:16]([CH3:18])[CH3:17])[NH:8]C(OC(C)(C)C)=O.[C:24]([OH:30])([C:26]([F:29])([F:28])[F:27])=[O:25]>C(Cl)Cl>[F:27][C:26]([F:29])([F:28])[C:24]([OH:30])=[O:25].[CH3:1][O:2][C:3](=[O:23])[C@H:4]([CH:20]([CH3:22])[CH3:21])[NH:5][C:6](=[O:19])[C@H:7]([CH:16]([CH3:17])[CH3:18])[NH2:8]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acid2 回HCID 13386190N-boc-l-valyl-l-valine methyl ester

生成物 1

HCID 86671346L-valyl L-valine methyl ester trifluoroacetate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

N-tert-butoxycarbonyl L-valyl L-valine methyl ester (16.47 g, 49.85 mmol) was treated with a 50% (v/v) solution of TFA in CH2Cl2 (130 mL). The reaction mixture was stirred for 2 h at room temperature before the solvent and bulk of excess TFA were evaporated. Portions of CH2Cl2 (3×100 mL) and purified CHCl3 (6×200 mL) were added and evaporated. The residue (19.17 g) was washed with Et2O (2×80 mL) and the Et2O decanted off. An additional 80 mL Et2O was added and the suspension filtered. The collected solid was washed with Et2O (80 mL) and dried; δH (300 MHz; d6-DMSO) 8.62 (1H, d, J 7, NH), 8.17 (3H, br s, NH3+), 4.19 (1H, dd, J 7 and 6, CαH(Val2)), 3.75 (1H, br d, J 5, CαH(Val1)), 3.64 (3H, s, OCH3), 2.16-2.01 (2H, m, CH(CH3)2), 0.96-0.90 (12H, m, CH(CH3)2); δC (75 MHz; d6-DMSO) 171.4, 168.4, 158.4 (q, JCF 31), 117.1 (q, JCF 297) 57.7, 56.9, 51.7, 29.9, 29.6, 18.8, 18.1, 18.1, 17.4

後処理

  1. customwere evaporated
  2. customPortions of CH2Cl2 (3×100 mL) and purified CHCl3 (6×200 mL)
  3. additionwere added
  4. customevaporated
  5. washThe residue (19.17 g) was washed with Et2O (2×80 mL)
  6. customthe Et2O decanted off
  7. additionAn additional 80 mL Et2O was added
  8. filtrationthe suspension filtered
  9. washThe collected solid was washed with Et2O (80 mL)
  10. customdried

出典と根拠

ORDレコード
ord-f00420c739bb4fdfa5e6255fa35d3a8e
出典データセット
uspto-grants-2016_01
特許番号
US09227995B2

反応ノート

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