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Hydrochloric Acid → 1-(Tert-butoxycarbonylamino-methyl)-6,8-dimethoxy-isoquinoline-4-carboxylic acid

HRID 14628
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HRID 14628 반응식
C([O:3][C:4]([C:6]1[C:15]2[C:10](=[C:11]([O:18][CH3:19])[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[C:9]([CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[N:8][CH:7]=1)=[O:5])C.O[Li].O.CCOC(C)=O.Cl>C1COCC1.O>[C:25]([O:24][C:22]([NH:21][CH2:20][C:9]1[C:10]2[C:15](=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])[C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]=1)=[O:23])([CH3:28])([CH3:26])[CH3:27]
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참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 593410801-(Tert-butoxycarbonylamino-methyl)-6,8-dimethoxy-isoquinoline-4-carboxylic acid ethyl ester

생성물 1

HCID 593410981-(Tert-butoxycarbonylamino-methyl)-6,8-dimethoxy-isoquinoline-4-carboxylic acid수율 96%

시약·촉매·용매 2

HCID 962Water용매2회
HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

To a solution of 1-(tert-butoxycarbonylamino-methyl)-6,8-dimethoxy-isoquinoline-4-carboxylic acid ethyl ester (520 mg, 1.34 mmol) in THF (10 ml) and H2O (10 ml) under nitrogen, LiOH—H2O (95 mg, 2.3 mmol) was added. The reaction was stirred at 50° C. for 3.5 hours and at then at room temperature for 18 hours. EtOAc and water were then added and the pH was adjusted to 5 by dropwise addition of 6N HCl. The layers were then separated and the aqueous phase was extracted with EtOAc. The combined organic layers were then washed with brine, dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure to give 1-(tert-butoxycarbonylamino-methyl)-6,8-dimethoxy-isoquinoline-4-carboxylic acid as a solid (464 mg, 96%). H1-NMR (DMSO): δ, 8.84 (s, 1H), 7.96 (s, 1H), 6.91 (t, 1H, J=5.4 Hz), 6.77 (s, 1H), 4.80 (d, 2H, J=5.43 Hz), 3.95 and 3.88 (s, 3H each), 1.36 (s, 9H).

후처리

  1. waitat then at room temperature for 18 hours
  2. customThe layers were then separated
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washThe combined organic layers were then washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-0ebda1cd5a5b46b19dc8d2e133fb3bbe
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07732446B1

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