Table 2 Action sequence extracted from an experimental procedure.
From: Automated extraction of chemical synthesis actions from experimental procedures
1 | MakeSolution with methyl 3-7-amino-2-[(2,4-dichlorophenyl)(hydroxy)methyl]-1H-benzimidazol-1-ylpropanoate (6.00 g, 14.7 mmol) and acetic acid (7.4 mL) and methanol (147 mL); |
2 | Add SLN; |
3 | Add acetaldehyde (4.95 mL, 88.2 mmol) at 0 °C; |
4 | Wait 30 min; |
5 | Add sodium acetoxyborohydride (18.7 g, 88.2 mmol); |
6 | Wait 2 h; |
7 | Quench with water; |
8 | Concentrate; |
9 | Add ethyl acetate; |
10 | Wash with aqueous sodium hydroxide (1 M); |
11 | Wash with brine; |
12 | DrySolution over sodium sulfate; |
13 | Filter keep filtrate; |
14 | Concentrate; |
15 | Purify; |
16 | Yield title compound (6.30 g, 13.6 mmol, 92%). |
