| 63% |
Stage #1: 3-fluorophthalic anhydride; L-glutamine In N,N-dimethyl-formamide at 20 - 90℃; for 2h;
Stage #2: With hydrogenchloride In water at 20℃; for 36h; |
1 Step 1 - 5-amino-2-(4-fluoro-1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid
To a stirred solution of 4-fluoroisobenzofuran-1,3-dione (25 g, 150 mmol, CASNo. 652-39-1) in DMF (100 mL) was added L-glutamine (22 g, 150 mmol) at rt. The resulting reaction mixture was heated to at 90 °C and stirred for 2 h. The reaction mixture was then evaporated under reduced pressure, transferred into 4 N aqueous HCl solution and the resulting mixture was stirred for 36 h at rt. The solid precipitate was then filtered off, washed with cold water and dried under reduced pressure to give 5-amino-2-(4-fluoro-1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid as a white solid (28 g, 63%). LC-MS (ESI+) m/z 295 (M+H)+. |
| 63% |
Stage #1: 3-fluorophthalic anhydride; L-glutamine In N,N-dimethyl-formamide at 90℃; for 2h; Inert atmosphere;
Stage #2: With hydrogenchloride In water at 20℃; for 36h; Inert atmosphere; |
1 [00843] Step 1 - 5-amino-2-(4-fluoro-1.3-dioxoisoindolin-2-yl)-5-oxopentanoic acid
[00844] To a stirred solution of 4-fluoroisobenzofuran- 1,3 -dione (25 g, 150 mmol, CASNo. 652-39-1) in DMF (100 mL) was added L-glutamine (22 g, 150 mmol) at rt. The resulting reaction mixture was heated to at 90 °C and stirred for 2 h. The reaction mixture was then evaporated under reduced pressure, transferred into 4 N aqueous HC1 solution and the resulting mixture was stirred for 36 h at rt. The solid precipitate was then fdtered off, washed with cold water and dried under reduced pressure to give 5-amino-2-(4-fluoro-1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid as a white solid (28 g, 63%). LC-MS (ESI+) m/z 295 (M+H)+. |
| 63% |
Stage #1: 3-fluorophthalic anhydride; L-glutamine In N,N-dimethyl-formamide at 90℃; for 2h; Inert atmosphere;
Stage #2: With hydrogenchloride In water at 20℃; for 36h; Inert atmosphere; |
1 Step 1 - 5-amino-2-(4-fluoro-1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid
To a stirred solution of 4-fluoroisobenzofuran-1,3-dione (25 g, 150 mmol, CAS 652-39-1) in DMF (100 mL) was added L-glutamine (22 g, 150 mmol) at rt. The resulting reaction mixture was heated to at 90 °C and stirred for 2 h. The reaction mixture was then evaporated under reduced pressure, transferred into 4 N aqueous HCl solution and the resulting mixture was stirred for 36 h at rt. The solid precipitate was then filtered off, washed with cold water and dried under reduced pressure to give 5-amino-2-(4-fluoro-1,3- dioxoisoindolin-2-yl)-5-oxopentanoic acid as a white solid (28 g, 63%). LC-MS (ESI+) m/z 295 (M+H)+. |
| 63% |
Stage #1: 3-fluorophthalic anhydride; L-glutamine In N,N-dimethyl-formamide at 90℃; for 2h; Inert atmosphere;
Stage #2: With hydrogenchloride In water at 20℃; for 36h; Inert atmosphere; |
1 Step 1 - 5-amino-2-(4-fluoro-1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid
To a stirred solution of 4-fluoroisobenzofuran-1,3-dione (25 g, 150 mmol, CAS 652-39-1) in DMF (100 mL) was added L-glutamine (22 g, 150 mmol) at rt. The resulting reaction mixture was heated to at 90 °C and stirred for 2 h. The reaction mixture was then evaporated under reduced pressure, transferred into 4 N aqueous HCl solution and the resulting mixture was stirred for 36 h at rt. The solid precipitate was then filtered off, washed with cold water and dried under reduced pressure to give 5-amino-2-(4-fluoro-1,3- dioxoisoindolin-2-yl)-5-oxopentanoic acid as a white solid (28 g, 63%). LC-MS (ESI+) m/z 295 (M+H)+. |
|
Stage #1: 3-fluorophthalic anhydride; L-glutamine In N,N-dimethyl-formamide at 90℃; for 8h;
Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide for 8h; |
1.B.1.2 Step 2: 5-amino-2-(4-fluoro-1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid
A mixture of the above 4-fluoroisobenzofuran-1,3-dione (40 g, crude) and L-glutamine (35 g, 239 mmol) in dry DMF (200 mL) was stirred at 90 for 8 h. The solvent was removed under reduced pressure. The residue was re-dissolved in 4N HCl (200 mL) and stirred for additional 8 h. The resulting precipitation was collected by filtration, washed with water, and dried to afford 5-amino-2-(4-fluoro-1,3-dioxoisoindolin-2-yl)-5-oxopentanoic acid (37 g, crude) as an off-white solid. LC-MS: 295.2 [MH]+.1H NMR (400 MHz, CDCl3): δ 2.16-2.20 (m.2H), 2.31-2.43 (m, 2H), 4.79-4.83 (m, 1H), 6.79 (br, 1H), 7.26(br, 1H), 7.77-7.85 (m, 2H), 7.98-8.03 (m, 1H), 13.32(br, 1H). |
|
In N,N-dimethyl-formamide at 90℃; |
|
| 63 % |
In N,N-dimethyl-formamide at 90℃; Inert atmosphere; |
Step 1 - 5-amino-2-(4-fluoro- 1.3-dio\oisoindolin-2-yl)-5-o\opcntanoic acid
To a stirred solution of 4-fluoroisobenzofuran-l,3-dione (25 g, 150 mmol, CAS 652-39-1) in DMF (100 mF) was added F-glutamine (22 g, 150 mmol) at rt. The resulting reaction mixture was heated to at 90 °C and stirred for 2 h. The reaction mixture was then evaporated under reduced pressure, transferred into 4 N aqueous HC1 solution and the resulting mixture was stirred for 36 h at rt. The solid precipitate was then filtered off, washed with cold water and dried under reduced pressure to give 5-amino-2-(4-fluoro-l,3- dioxoisoindolin-2-yl)-5-oxopentanoic acid as a white solid (28 g, 63%). FC-MS (ESU) m/z 295 (M+H)+. |
| 63 % |
In N,N-dimethyl-formamide at 90℃; Inert atmosphere; |
Step 1 - 5-amino-2-(4-fluoro- 1.3-dio\oisoindolin-2-yl)-5-o\opcntanoic acid
To a stirred solution of 4-fluoroisobenzofuran-l,3-dione (25 g, 150 mmol, CAS 652-39-1) in DMF (100 mF) was added F-glutamine (22 g, 150 mmol) at rt. The resulting reaction mixture was heated to at 90 °C and stirred for 2 h. The reaction mixture was then evaporated under reduced pressure, transferred into 4 N aqueous HC1 solution and the resulting mixture was stirred for 36 h at rt. The solid precipitate was then filtered off, washed with cold water and dried under reduced pressure to give 5-amino-2-(4-fluoro-l,3- dioxoisoindolin-2-yl)-5-oxopentanoic acid as a white solid (28 g, 63%). FC-MS (ESU) m/z 295 (M+H)+. |
| 70 % |
In N,N-dimethyl-formamide at 90℃; |
|
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