Triethylamine → HCID 59548956, 화합물

HRID 1895616노트

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HRID 1895616 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:29][C:30]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:31]=1[F:38])[CH2:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]2[C:19]([C:25]([F:28])([F:27])[F:26])=[N:20][C:21]([C:22]([OH:24])=[O:23])=[C:15]2[CH2:14]1)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:40][CH2:41][C:42]([O:44][CH3:45])=[O:43].C(N(CC)CC)C.O=C1N([ClH:59]P([ClH]N2CCOC2=O)=O)CCO1>ClCCl>[ClH:59].[CH3:45][O:44][C:42](=[O:43])[CH2:41][NH:40][C:22]([C:21]1[N:20]=[C:19]([C:25]([F:26])([F:27])[F:28])[N:16]2[CH2:17][CH2:18][N:13]([C:11](=[O:12])[CH2:10][C@H:9]([NH2:8])[CH2:29][C:30]3[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:31]=3[F:38])[CH2:14][C:15]=12)=[O:24].[CH3:45][O:44][C:42](=[O:43])[CH2:41][NH:40][C:22]([C:21]1[N:20]=[C:19]([C:25]([F:27])([F:28])[F:26])[N:16]2[CH2:17][CH2:18][N:13]([C:11](=[O:12])[CH2:10][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:29][C:30]3[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:31]=3[F:38])[CH2:14][C:15]=12)=[O:23]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 59548952(R)-7-[3-tert-butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid

생성물 2

HCID 44194134(R)-({7-[3-Amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carbonyl}-amino)-acetic acid methyl ester hydrochlorideHCID 59548956HCID 59548956, 화합물수율 107.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(R)-7-[3-tert-Butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid 2a (150 mg, 0.27 mmol) and methyl glycinate hydrochloride (512 mg, 0.408 mmol) were dissolved in 8 mL of dichloromethane under stirring, and triethylamine (0.25 mL, 1.62 mmol) was then added to the solution. After stirring for 5 minutes, bis(2-oxo-3-oxazolidinyl)phosphonic chloride (0.138 g, 0.54 mmol) was added. The reaction mixture was reacted at room temperature for 20 hours and monitored by thin layer chromatography until the disappearance of the starting materials. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (R)-({7-[3-tert-butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carbonyl}-amino)-acetic acid methyl ester 16a (90 mg, yield 53.6%) as a light yellow oil.

후처리

  1. stirringAfter stirring for 5 minutes
  2. customThe reaction mixture was reacted at room temperature for 20 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-bdaeef327cb041aa8c09a53f97239956
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513411B2

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