Phenethylamine → HCID 14444045、化合物

HRID 1457826ノート

反応式

HRID 1457826 の反応式
[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:2]([C:14]([OH:16])=O)[CH2:3][C:4](=[O:13])[O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CN1CCOCC1.C(OC(Cl)=O)C(C)C.[CH2:39]([NH2:47])[CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1COCC1>[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:2]([C:14]([NH:47][CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:16])[CH2:3][C:4](=[O:13])[O:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

参加物

6

反応物 4

HCID 1001PhenethylamineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 1581888N-tert-Butoxycarbonyl-L-aspartic acid beta-benzyl ester

生成物 1

HCID 14444045HCID 14444045、化合物収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-15 °C

実験手順

To a stirred solution of Boc-Asp(OBzl), 5.0 g (15.5 mmol) and N-methyl morpholine (15.5 mmol) in 50 mL of dry THF under an Ar atmosphere was added isobutylchloroformate (15.5 mmol) at -15° C. After a few minutes, phenethylamine 2.0 mL (15.5 mmol) in 15 mL of dry THF was added. The mixture was maintained at -15° C. for 15 min. and allowed to warm to room temperature. After stirring for an additional 2 hours, the reaction mixture was filtered and the filtrate was concentrated in vacuo to dryness. The resulting residue was dissolved in ethyl acetate (100 mL) and washed successively with 1M HCl (2×50 mL), water (50 mL), 10% sodium carbonate (2×50 mL), and brine (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated to yield 5.59 gm (85%) of an amorphous white solid.

後処理

  1. waitAfter a few minutes
  2. temperatureto warm to room temperature
  3. filtrationthe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo to dryness
  5. dissolutionThe resulting residue was dissolved in ethyl acetate (100 mL)
  6. washwashed successively with 1M HCl (2×50 mL), water (50 mL), 10% sodium carbonate (2×50 mL), and brine (50 mL)
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-2ce30356ac6c4ce793bdb1f65b91533b
出典データセット
uspto-grants-1998_12
特許番号
US05849690

反応ノート

読み込み中…