Sodium Hydroxide → 9-Bromo-10-fluoro-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

HRID 926260노트

반응식

HRID 926260 반응식
[Br:1][C:2]1[C:11]([F:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:17](=[O:27])[CH2:18][NH:19][C:20](OC(C)(C)C)=[O:21])[CH:7]2[CH2:13]C(O)=O.BrC1C(F)=CC=C2C=1CCN(C(=O)CNC(OC(C)(C)C)=O)C2CC(OC)=O.[OH-].[Na+]>CCO>[Br:1][C:2]1[C:11]([F:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]1[C:17](=[O:27])[CH2:18][NH:19][C:20](=[O:21])[CH:13]=[C:7]12

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 86711337Methyl 2-(5-bromo-2-(2-((tert-butoxycarbonyl)amino)acetyl)-6-fluoro-1,2,3,4-tetrahydroisoquinolin-1-yl)acetateHCID 867113382-(5-Bromo-2-(2-((tert-butoxycarbonyl)amino)acetyl)-6-fluoro-1,2,3,4-tetrahydroisoquinolin-1-yl)acetic acid

생성물 1

HCID 867113419-Bromo-10-fluoro-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

2-(5-bromo-2-(2-((tert-butoxycarbonyl)amino)acetyl)-6-fluoro-1,2,3,4-tetrahydroisoquinolin-1-yl)acetic acid. To a stirred solution of methyl 2-(5-bromo-2-(2-((tert-butoxycarbonyl)amino)acetyl)-6-fluoro-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate (62.6 g, 136 mmol) in EtOH (500 mL), 4N aqueous NaOH (39.5 mL, 158 mmol) was added and the solution was stirred at RT for 2 h. The white precipitate was filtered off and the white solid was washed with a small amount of EtOH (1×) and diethyl ether (2×). The sodium salt was partitioned between 0.5N aqueous HCl and DCM, the organic layer was separated and washed with 0.5N aqueous HCl (1×) and brine (1×). The combined organic layers were dried with sodium sulfate, filtered and the solvent was removed under reduced pressure. The residue was dried under high vacuo overnight to yield the title compound as white foam (58.45 g). UPLC-MS: MS 445.2/447.2 (M+H+); UPLC rt 0.99 min.

후처리

  1. filtrationThe white precipitate was filtered off
  2. washthe white solid was washed with a small amount of EtOH (1×) and diethyl ether (2×)
  3. customThe sodium salt was partitioned between 0.5N aqueous HCl and DCM
  4. customthe organic layer was separated
  5. washwashed with 0.5N aqueous HCl (1×) and brine (1×)
  6. dry with materialThe combined organic layers were dried with sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was dried under high vacuo overnight

출처 및 근거

ORD 기록
ord-2ae10517f8804e2a881a75df99de775c
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284331B2

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