홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Dicyclohexylcarbodiimide → N-(4-Morpholinylsulfonyl)-L-phenylalanyl-3-(2-amino-4-thiazolyl)-L-alanine methyl ester monohydrochloride

HRID 1534639
노트
인쇄 미리보기

반응식

HRID 1534639 반응식
[ClH:1].Cl.[CH3:3][O:4][C:5](=[O:15])[C@H:6]([CH2:8][C:9]1[N:10]=[C:11]([NH2:14])[S:12][CH:13]=1)[NH2:7].[N:16]1([S:22]([NH:25][C@H:26]([C:34](O)=[O:35])[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:24])=[O:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C.C(N(CC)CC)C.CN(C)C=O>[ClH:1].[CH3:3][O:4][C:5](=[O:15])[C@H:6]([CH2:8][C:9]1[N:10]=[C:11]([NH2:14])[S:12][CH:13]=1)[NH:7][C:34](=[O:35])[C@H:26]([CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[NH:25][S:22]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)(=[O:24])=[O:23]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 10859978(2S)-2-[(4-morpholinylsulfonyl)amino]-3-phenylpropanoic acidHCID 867454923-(2-Amino-4-thiazolyl)-L-alanine methyl ester dihydrochlorideHCID 178418300HCID 178418300, 화합물

생성물 1

HCID 86745491N-(4-Morpholinylsulfonyl)-L-phenylalanyl-3-(2-amino-4-thiazolyl)-L-alanine methyl ester monohydrochloride

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매2회

반응 조건

온도
5 °C

실험 절차

3-(2-Amino-4-thiazolyl)-L-alanine methyl ester dihydrochloride, 12 kg (43.8 mol), 13.8 kg of N-(4-morpholinylsulfonyl)-L-phenylalanine (European Published Patent Application 0399556), 6.0 kg of hydroxybenzotriazole (HOBT), and 110 L of dimethylformamide are charged into a 800 L reactor and cooled to 5° C. Triethylamine, 9.4 kg, is charged over 10 minutes and cooled to 5° C. A solution of 9.5 kg of dicyclohexylcarbodiimide in 350 L of ethyl acetate is charged into the reaction mixture over a 15 minute period at 5° C. The slurry is allowed to warm to room temperature and stirred overnight. The slurry is diluted with 424 L of ethyl acetate and filtered. The cake is washed with 50 L of ethyl acetate. The filtrate is washed with water (2×140 L) and saturated sodium bicarbonate solution (2×150 L). The solution is diluted with 193 L of isopropyl alcohol. After cooling to 5° C., anhydrous hydrogen chloride gas (3.2 kg) is added to precipitate the product. After isolation by filtration, the product is dried at 25° C. under vacuum to give 18 kg of N-(4-morpholinyl-sulfonyl)-L-phenylalanyl-3-(2-amino-4-thiazolyl)-L-alanine methyl ester monohydrochloride as a white solid, 99.6% pure by HPLC; mass spectrum (chemical ionization) 498 M+H.

후처리

  1. temperaturecooled to 5° C
  2. temperatureto warm to room temperature
  3. filtrationfiltered
  4. washThe cake is washed with 50 L of ethyl acetate
  5. washThe filtrate is washed with water (2×140 L) and saturated sodium bicarbonate solution (2×150 L)
  6. additionThe solution is diluted with 193 L of isopropyl alcohol
  7. temperatureAfter cooling to 5° C.
  8. additionanhydrous hydrogen chloride gas (3.2 kg) is added
  9. customto precipitate the product
  10. filtrationAfter isolation by filtration
  11. customthe product is dried at 25° C. under vacuum

출처 및 근거

ORD 기록
ord-4017c25442bd43098e9c83624b971f4b
출처 데이터셋
uspto-grants-1992_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05089616

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트