Hydrochloric Acid → 9-Bromo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione
反応式
[Br:1][C:2]1[CH:11]=[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[CH2:12]C(OC)=O.BrC1C=CC=C2C=1CCNC2CC(OC)=O.C(NCC(O)=O)(OC(C)(C)C)=O.C(N(CC)CC)C.Cl>CCOC(C)=O.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>[Br:1][C:2]1[CH:11]=[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:12]=[C:7]12参加物
反応物 5
生成物 1
試薬・触媒・溶媒 2
実験手順
methyl 2-(5-bromo-2-(2-((tert-butoxycarbonyl)amino)acetyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate. To a stirred solution of methyl 2-(5-bromo-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate (76 g, 267 mmol), Boc-glycine (51.5 g, 294 mmol) and triethylamine (74.6 mL, 535 mmol) in AcOEt (1350 mL), T3P (191 mL, 321 mmol, 50% m/m in AcOEt) was added and the solution was stirred at RT for 90 min. 0.2N aqueous HCl (400 mL) was added and the reaction mixture was stirred for 5 min. The organic layer was separated and washed with 0.2N aqueous HCl (1×250 mL), saturated aqueous NaHCO3 (2×250 mL) and brine (1×250 mL). 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 (113 g) which was used without further purification. UPLC-MS: MS 441.2/443.2 (M+H+); UPLC rt 1.12 min.
後処理
- stirringthe reaction mixture was stirred for 5 min
- customThe organic layer was separated
- washwashed with 0.2N aqueous HCl (1×250 mL), saturated aqueous NaHCO3 (2×250 mL) and brine (1×250 mL)
- dry with materialThe combined organic layers were dried with sodium sulfate
- filtrationfiltered
- customthe solvent was removed under reduced pressure
- customThe residue was dried under high vacuo overnight
出典と根拠
- ORDレコード
- ord-62634818ebc2416d9cb27ea294e7a3e6
- 出典データセット
- uspto-grants-2014_10
- 特許番号
- US08853203B2
反応ノート
読み込み中…