Hydrochloric Acid → HCID 67285910, 화합물

HRID 1484095노트

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HRID 1484095 반응식
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].Cl.CN1CCOCC1.[N:23]1[CH:28]=[CH:27][N:26]=[CH:25][C:24]=1[C:29]([NH:31][C@H:32]([C:40](O)=[O:41])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:30].C1(N=C=NC2CCCCC2)CCCCC1.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH:6][C:40](=[O:41])[C@H:32]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[NH:31][C:29]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][N:23]=1)=[O:30]

참가 물질

8

반응물 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 75736Methyl L-phenylalaninate hydrochloride2회HCID 757711-HydroxybenzotriazoleHCID 15042559N-(Pyrazinylcarbonyl)-L-phenylalanine

생성물 1

HCID 67285910HCID 67285910, 화합물수율 95.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

L-phenylalanine methyl ester hydrochloride (0.8 g, 3.69 mmol) was dissolved with 20 ml of THF, then the hydrochloric acid was neutralized with NMM (0.49 ml, 4.43 mmol), cooled with an ice bath for later use. N-Pyrazineformyl-L-phenylalanine (1.0 g, 3.69 mmol) of Preparation example 3 was added to another reaction flask, dissolved with 20 ml of THF, and cooled with an ice water bath, dicyclohexylcarbodiimide (DCC) (0.76 g, 3.69 mmol), HOBt (0.60 g, 4.42 mmol) were added at 0° C. and reacted for 40 min at 0° C., then the solution of L-phenylalanine methyl ester hydrochloride in THF prepared, cooled and neutralized according to the above was added, the reaction was monitored by TLC and completed after 2 h, insoluble DCU was removed by filtration, to the filtrate was added 80 ml of ethyl acetate, washed with 5% sodium bicarbonate solution, 10% citric acid solution, 5% sodium bicarbonate solution, saturated salt solution (2×20 ml) successively. The ethyl acetate layer was dried over anhydrous sodium sulfate, filtered, and evaporated the solvent under reduced pressure, 1.52 g of white solid was obtained with a yield of 95.6%, m.p.: 111˜113° C. 1H-NMR (CDCl3, 300 MHz): δ 3.04 (—CH2, m, 2H), 3.18 (—CH2, d, 2H), 3.69 (—CH3, s, 3H), 4.82 (—CH, m, 2H), 6.36 (—CONH, d, 1H), 6.92˜7.30 (-Ph, m, 10H), 8.26 (—CONH, d, 1H), 8.54 (-Pyz, d, 1H), 8.76 (-Pyz, d, 1H), 9.33 (-Pyz, s, 1H).

후처리

  1. temperaturecooled with an ice bath for later use
  2. additionwas added to another reaction flask
  3. temperaturecooled with an ice water bath
  4. customreacted for 40 min at 0° C.
  5. temperaturecooled
  6. additionabove was added
  7. custominsoluble DCU was removed by filtration, to the filtrate
  8. additionwas added 80 ml of ethyl acetate
  9. washwashed with 5% sodium bicarbonate solution, 10% citric acid solution, 5% sodium bicarbonate solution, saturated salt solution (2×20 ml) successively
  10. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. customevaporated the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-5d1cba388ee54144a8f59bd5bcb42b49
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09421237B2

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