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1-Hydroxybenzotriazole → [3-(2-Amino-3-nitro-phenylcarbamoyl)-propyl]methyl-carbamic acid tert-butyl ester
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 1-Hydroxybenzotriazole | HCID 75771 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | Sodium Bicarbonate | HCID 516892 | — |
| 反応物 | 3-Nitro-1,2-phenylenediamine | HCID 4359525 | — |
| 反応物 | 4-{[(Tert-butoxy)carbonyl](methyl)amino}butanoic acid | HCID 10656390 | — |
| 溶媒 | 1,2-Dichloroethane | HCID 11 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | [3-(2-Amino-3-nitro-phenylcarbamoyl)-propyl]methyl-carbamic acid tert-butyl ester | HCID 68412474 | 37% |
反応手順
To a solution of 9 g of 4-(tert-butoxycarbonyl-methyl-amino)-butyric acid (prepared from 4-(methylamino)butyric acid and BOC anhydride) in 159 mL DCM were added 14.2 mL of DIPEA, 8 g of HOBt and 9.1 g of EDC. After stirring for 5 min 6.1 g of 3-nitro-benzene-1,2-diamine were added and the mixture was stirred for 4 days at rt. Saturated aq. NaHCO3 solution was added, the phases were separated and the organic phase washed with brine. The combined organic phases were dried over MgSO4, and concentrated in vacuo. Purification by CC using EtOAc/heptane 1/4 to 3/1 yielded 5.2 g of [3-(2-Amino-3-nitro-phenylcarbamoyl)-propyl]methyl-carbamic acid tert-butyl ester as orange foam.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08202885B2 |
| 出典データセット | uspto-grants-2012_06 |
| ORD ID | ord-8d476292571949feb02165cc8d6ed4e2 |
| 出典メモ | uspto-grants-2012_06 |