Hydrochloric Acid → HCID 86597003, 화합물

HRID 1180724노트

반응식

HRID 1180724 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 86597003HCID 86597003, 화합물수율 91%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9e7916c3a4de4708944ed3bc6b39b6e1
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282512B2

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