Acetic Acid → HCID 68929321, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:24])=[C:11]([CH2:13][C:14]([NH:16][CH2:17][C@@H:18]3[O:23][CH2:22][CH2:21][NH:20][CH2:19]3)=[O:15])[N:12]=2)=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][CH:34]=O)=[CH:28][CH:27]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][CH2:34][N:20]2[CH2:21][CH2:22][O:23][C@@H:18]([CH2:17][NH:16][C:14](=[O:15])[CH2:13][C:11]3[N:12]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[O:9][C:10]=3[CH3:24])[CH2:19]2)=[CH:28][CH:27]=1Participants
6
Conditions
- Temperature
- 20 °C
Procedure
A mixture of Intermediate 28 (0.04 g), 3-(4-chlorophenyl)propanal (0.026 g) and acetic acid (0.02 ml) in dichloromethane (4 ml) was treated with sodium triacetoxyborohydride (0.080 g). The mixture was stirred at 20° C. for 72 h. The mixture was partitioned between chloroform (6 ml) and saturated aqueous sodium hydrogen carbonate (6 ml). The phases were separated and the organic phase applied to an ion exchange cartridge (2 g Isolute SCX, prewashed with methanol). The SCX cartridge was eluted with methanol (10 ml) followed by 10% 0.880 ammonia in methanol (10 ml) and the appropriate fractions were concentrated in vacuo to give the title compound as a colourless gum (0.055 g).
Workup
- customThe mixture was partitioned between chloroform (6 ml) and saturated aqueous sodium hydrogen carbonate (6 ml)
- customThe phases were separated
- washThe SCX cartridge was eluted with methanol (10 ml)
- concentrationthe appropriate fractions were concentrated in vacuo
Sources & evidence
- ORD record
- ord-aeac264788994ec7bb14cb30e9323532
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07101882B2
Reaction notes
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