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Hydrochloric Acid → HCID 89812813, 화합물

HRID 1481115
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HRID 1481115 반응식
CO[C:3]([C:5]1[N:6]=[C:7]([C:23]#[N:24])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[NH2:25][C@H:26]([CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:27][C:28]([OH:30])=[O:29].C[O-].[Na+].CO.Cl>O>[C:23]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:9]=2)[C:14]([OH:15])=[C:5]([C:3]([NH:25][C@H:26]([CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:27][C:28]([OH:30])=[O:29])=[O:4])[N:6]=1)#[N:24]
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참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 7009759(r)-3-Amino-5-phenylpentanoic acidHCID 23694274Sodium methanolate methanolHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

생성물 1

HCID 89812813HCID 89812813, 화합물수율 43%

시약·촉매·용매 1

HCID 962
Water
용매

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온도
130 °C

실험 절차

1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (75 mg, 0.234 mmol) and 3-(R)-Amino-5-phenyl-pentanoic acid (193 mg, 1.0 mmol) were placed in a CEM 10 mL Microwave vessel and sodium methoxide-methanol solution (0.5 M; 2.0 mL, 1.0 mmol) was added via syringe. The vessel was sealed and heated to 130° C. in a CEM microwave apparatus for 4.5 hours. The reaction mixture was diluted with water and treated with 1N hydrochloric acid and extracted three times with ethyl acetate then dried over sodium sulfate. The crude product was purified by MPLC (methylene chloride-methanol) to provide the title compound as an off-white solid in 43% yield. MS ESI(−) m/e: 480.1305 (M−1).

후처리

  1. additionwas added via syringe
  2. customThe vessel was sealed
  3. extractionextracted three times with ethyl acetate
  4. dry with materialthen dried over sodium sulfate
  5. customThe crude product was purified by MPLC (methylene chloride-methanol)

출처 및 근거

ORD 기록
ord-1939de1f1ff845099fa057dba18857ab
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09409892B2

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