4-Methylmorpholine → HCID 178501380、化合物

HRID 2268801ノート

反応式

HRID 2268801 の反応式
Cl.[CH3:2][O:3][C:4](=[O:24])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:23])=[CH:10][CH:9]=1)[NH2:6].[SH:25][C:26]1[N:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28](O)=[O:29].CN1CCOCC1>CN(C=O)C>[CH3:2][O:3][C:4](=[O:24])[C@H:5]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:15][C:16]2[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:23])=[CH:12][CH:13]=1)[NH:6][C:28](=[O:29])[C:27]1[CH:31]=[CH:32][CH:33]=[N:34][C:26]=1[SH:25]

参加物

5

反応物 3

HCID 79724-MethylmorpholineHCID 69806827HCID 69806827、化合物HCID 178524460HCID 178524460、化合物

生成物 1

HCID 178501380HCID 178501380、化合物収率 93%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of O-(2,6dichlorobenzyl)-L-tyrosine methyl ester hydrochloride (2.50 g, 6.4 mmol), 2-mercaptonicotinic acid (0.99 g, 6.4 mmol) and NMM (1.41 ml, 1.29 g, 12.8 mmol) in DMF (10 ml) was stirred at room temperature for 64 h. Solvent was removed in vacuo and the residue partitioned between DCM (30 ml) and water (25 ml). The aqueous layer was extracted with DCM (30 ml) and the combined organic layers were washed with 10% NaHCO3 solution (30 ml), dried over MgSO4 and the solvent removed in vacuo to give a brown oil which was purified by chromatography (SiO2; gradient elution, 4:1 EtOAc/hexane to 100% EtOAc) to give the title compound as a yellow foam, (2.92 g, 93%). δH (CDCl3) 8.71 (1H, dd, J 1.8, 7.6Hz), 8.05 (1H, s), 7.61 (1H, dd, J 1.8, 6.1 Hz), 7.35 (2H, m), 7.33-7.19 (2H, m), 6.94 (2H, d, J 8.7Hz), 5.22 (2H, s), 4.97 (1H, m), 3.74 (3H, s) and 3.21 (2H, m).

後処理

  1. customSolvent was removed in vacuo
  2. customthe residue partitioned between DCM (30 ml) and water (25 ml)
  3. extractionThe aqueous layer was extracted with DCM (30 ml)
  4. washthe combined organic layers were washed with 10% NaHCO3 solution (30 ml)
  5. dry with materialdried over MgSO4
  6. customthe solvent removed in vacuo
  7. customto give a brown oil which
  8. customwas purified by chromatography (SiO2; gradient elution, 4:1 EtOAc/hexane to 100% EtOAc)

出典と根拠

ORDレコード
ord-9eb107e6a3854fcdb45b2041f0372392
出典データセット
uspto-grants-2001_12
特許番号
US06329372B1

反応ノート

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