Triethylamine → {1-[2-(4-Nitrophenyl)-ethyl]-2-oxopyrrolidin-3-(s)-yl}-carbamic acid tert-butyl ester

HRID 651624ノート

反応式

HRID 651624 の反応式
[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:2]([C:7](OCC1C=CC=CC=1)=[O:8])[CH2:3][C:4](=O)O.Cl.[N+:25]([C:28]1[CH:36]=[CH:35][C:31]([CH2:32][CH2:33][NH2:34])=[CH:30][CH:29]=1)([O-:27])=[O:26].C(N(CC)CC)C.C([BH3-])#N.[Na+].[OH-].[Na+]>CO.O>[C:20]([O:19][C:17](=[O:18])[NH:1][C@H:2]1[CH2:3][CH2:4][N:34]([CH2:33][CH2:32][C:31]2[CH:30]=[CH:29][C:28]([N+:25]([O-:27])=[O:26])=[CH:36][CH:35]=2)[C:7]1=[O:8])([CH3:21])([CH3:22])[CH3:23]

参加物

8

反応物 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 458983Benzeneethanamine, 4-nitro-, hydrochloride (1:1)HCID 5003444Sodium cyanoborohydrideHCID 7017887(3S)-4-(benzyloxy)-3-(((tert-butoxy)carbonyl)amino)-4-oxobutanoic acid

生成物 1

HCID 54464437{1-[2-(4-Nitrophenyl)-ethyl]-2-oxopyrrolidin-3-(s)-yl}-carbamic acid tert-butyl ester収率 39.1%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a solution of Boc-L-Asp(H)-OBn (3.3 g, 10.7 mmol) dissolved in methanol (50 mL) is added 4 Å molecular sieves, 4-nitrophenethylamine hydrochloride (4.35 g, 21.5 mmol) and triethylamine (2.25 g, 22.2 mmol). The solution is stirred at room temperature for 45 minutes and then the mixture is treated with sodium cyanoborohydride (0.72 g, 11.5 mmol). The reaction mixture is stirred at room temperature for 16 hours. After this time,1 N NaOH (10 mL) followed by water (25 mL) is added. The resulting mixture is stirred for 30 minutes and then concentrated in vacuo to a smaller volume. The solution is diluted with EtOAc (250 mL), filtered through a pad of Celite and washed with water and EtOAc. The solution is poured into a separatory funnel and the layers are separated. The aqueous layer is extracted with EtOAc. The combined organic layers are washed with 1N HCl, H2O, saturated NaHCO3 solution and saturated NaCl. The organic phase is dried over MgSO4, filtered and concentrated. The crude residue is purified by column chromatography eluting with 50% EtOAc/CH2Cl2 to afford the title compound (1.46 g, 4.18 mmol) as a pale yellow solid.

後処理

  1. stirringThe reaction mixture is stirred at room temperature for 16 hours
  2. additionis added
  3. stirringThe resulting mixture is stirred for 30 minutes
  4. concentrationconcentrated in vacuo to a smaller volume
  5. additionThe solution is diluted with EtOAc (250 mL)
  6. filtrationfiltered through a pad of Celite
  7. washwashed with water and EtOAc
  8. additionThe solution is poured into a separatory funnel
  9. customthe layers are separated
  10. extractionThe aqueous layer is extracted with EtOAc
  11. washThe combined organic layers are washed with 1N HCl, H2O, saturated NaHCO3 solution and saturated NaCl
  12. dry with materialThe organic phase is dried over MgSO4
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customThe crude residue is purified by column chromatography
  16. washeluting with 50% EtOAc/CH2Cl2

出典と根拠

ORDレコード
ord-28ec7242ea3b4dcc974796f7ec4ee00f
出典データセット
uspto-grants-2001_08
特許番号
US06281227B1

反応ノート

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