Acetaldehyde → Benzyl-N-(1-cyanoethyl)glycine hydrochloride

HRID 1016254

反応式

HRID 1016254 の反応式
C[Si]([C:5]#[N:6])(C)C.[CH2:7]([NH:14][CH2:15][C:16]([OH:18])=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH:19](=O)[CH3:20].[Cl:22]CCl>>[ClH:22].[CH2:7]([N:14]([CH:19]([C:5]#[N:6])[CH3:20])[CH2:15][C:16]([OH:18])=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

5

反応物 4

HCID 177AcetaldehydeHCID 6344DichloromethaneHCID 82115Trimethylsilyl cyanideHCID 869652-(Benzylamino)acetic acid

生成物 1

HCID 68560147Benzyl-N-(1-cyanoethyl)glycine hydrochloride

実験手順

Trimethylsilyl cyanide (4.0 mL, 30 mmol) was added cautiously to a stirred solution of benzyl glycine free base (5.0 g, 30 mmol) and acetaldehyde (1.7 mL, 30 mmol) in dichloromethane (15 mL) under argon atmosphere. After 15 hours, the volatile components were removed in vacuo, and the residue was dissolved in ethyl acetate (200 mL), washed with brine (100 mL), dried (Na2SO4) and evaporated to an oil. The oil was redissolved in ether (30 mL) and ethanol (30 mL), and 1 M HCl in ether (33 mL) was added dropwise to give the title compound as an off-white crystalline precipitate (6.60 g, 100%). mp: 137-138° C. 1H NMR (CD3OD) δ 7.31-7.48 (m, 5H), 5.32 (s, 2H), 4.68 (q, 1H, J=7.0 Hz), 4.22 (s, 2H), 1.73 (d, 3H, J=7.1 Hz). CI MS m/z=192 (M+H). Anal. Calcd. for C12H14N2O2.HCl: C, 56.49; H, 5.95; N, 11.00. Found: C, 56.32; H, 5.88; N, 10.89.

後処理

  1. customthe volatile components were removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  3. washwashed with brine (100 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated to an oil
  6. dissolutionThe oil was redissolved in ether (30 mL)
  7. additionethanol (30 mL), and 1 M HCl in ether (33 mL) was added dropwise

出典と根拠

ORDレコード
ord-013c8dd70bc64e8d96ba972bcfd53ea5
出典データセット
uspto-grants-2002_11
特許番号
US06476016B2

関連ノート

読み込み中…