Hydrochloric Acid → HCID 86597003、化合物

HRID 1180724ノート

反応式

HRID 1180724 の反応式
Cl.[NH2:2][C@@H:3]([CH2:8][CH2:9][CH2:10][CH3:11])[C:4]([O:6][CH3:7])=[O:5].N1C=CC=CC=1.[C:18](Cl)(Cl)=[O:19].Cl>ClCCl.C1(C)C=CC=CC=1>[N:2]([C@@H:3]([CH2:8][CH2:9][CH2:10][CH3:11])[C:4]([O:6][CH3:7])=[O:5])=[C:18]=[O:19]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6371PhosgeneHCID 14039065methyl (2S)-2-aminohexanoate hydrochloride

生成物 1

HCID 86597003HCID 86597003、化合物収率 91%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To 25.00 g (137.62 mmol) of methyl(2S)-2-aminohexanoate hydrochloride in 458 mL of dichloromethane at 0° C. was added 44.52 mL (550.49 mmol) of pyridine. Then, 85.57 mL (165.14 mmol) of a 1.93 M solution of phosgene in toluene was added to the solution and the mixture was stirred at 0° C. for 3 h. The solution was poured into 1N hydrochloric acid at 0° C. and extracted with dichloromethane. The organic layer was washed with 1N hydrochloric acid and saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The residue was purified by vacuum distillation at 80° C. @ 2 torr to give 21.32 g (91%) of methyl(2S)-2-isocyanatohexanoate. Rf=0.46 (1:4 ethyl acetate:hexanes); 1H NMR (300 MHz, DMSO-d6)δ 4.37 (dd, J=7 Hz, J=5 Hz, 1H), 3.73 (s, 3H), 1.78-1.60 (m, 2H), 1.36-1.16 (m, 4H), 0.85 (t, J=7 Hz, 3H); ES-MS m/z 172 (M+H).

後処理

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with 1N hydrochloric acid and saturated sodium chloride
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. distillationThe residue was purified by vacuum distillation at 80° C. @ 2 torr

出典と根拠

ORDレコード
ord-9e7916c3a4de4708944ed3bc6b39b6e1
出典データセット
uspto-grants-2007_10
特許番号
US07282512B2

反応ノート

読み込み中…