Sodium hydride → N-(4-Cyanobenzyl)-L-pyroglutamic acid methyl ester

HRID 55116

反応式

HRID 55116 の反応式
[CH3:1][O:2][C:3](=[O:10])[C@@H:4]1[CH2:8][CH2:7][C:6](=[O:9])[NH:5]1.[H-].[Na+].[C:13]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1)#[N:14]>C1COCC1>[CH3:1][O:2][C:3](=[O:10])[C@@H:4]1[CH2:8][CH2:7][C:6](=[O:9])[N:5]1[CH2:19][C:18]1[CH:21]=[CH:22][C:15]([C:13]#[N:14])=[CH:16][CH:17]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 78646Methyl 5-oxo-L-prolinateHCID 869964-(Bromomethyl)benzonitrile

生成物 1

HCID 54410854N-(4-Cyanobenzyl)-L-pyroglutamic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

L-Pyroglutamic acid methyl ester (1.36 g, 0.0095 mol) was dissolved in dry THF (20 mL) under Ar, treated with NaH (60% oil dispersion) (0.58 g, 0.0145 mol) with stirring for 5 min, then the mixture was cooled to 0° C. p-Cyanobenzylbromide (1.78 g, 0.0091 mol) was added, and the mixture left to slowly warm to ambient temperature. After 48 h the reaction mixture was partitioned between EtOAc and satd NaHCO3 solution, the aqueous layer separated and washed with CH2Cl2, the organics combined, washed with brine and dried (MgSO4). Filtration and concentration to dryness followed by trituration with ether gave the white solid product. 1H NMR(CDCl3, 400 MHz) δ 7.62(2H, d, J=8 Hz), 7.33(2H, d, J=8 Hz), 4.98(1H, d, J=15.4 Hz), 4.13(1H, d, J=15.4 Hz), 3.99(1H, dd, J=3, 9 Hz) and 2.5-2.6 (1H, m), 2.4-2.5 (1H, m), 2.2-2.45 (1H, m), 2.1-2.2 (1H, m) ppm.

後処理

  1. additionwas added
  2. waitthe mixture left
  3. customAfter 48 h the reaction mixture was partitioned between EtOAc and satd NaHCO3 solution
  4. customthe aqueous layer separated
  5. washwashed with CH2Cl2
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationFiltration and concentration to dryness
  9. customgave the white solid product

出典と根拠

ORDレコード
ord-d18623d16e6b413aa46d8681ce67e225
出典データセット
uspto-grants-1997_04
特許番号
US05624936

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