Formic Acid → (2R)-2-({N-formyl-N-benzoxy-amino}methyl)-7-octenoic acid
Reaction equation
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[CH2:11]([O:18][NH:19][CH2:20][C@@H:21]([CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH2:30])[C:22]([OH:24])=[O:23])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl>[CH:1]([N:19]([CH2:20][C@@H:21]([CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH2:30])[C:22]([OH:24])=[O:23])[O:18][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:2]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a cold solution of HCO2H (3.2 mL) and dichloromethane (10 mL) at 0° C. was added acetic anhydride (1.2 mL, 12.9 mmol). The mixture was stirred for 1 hour at 0° C. To the resulting mixture was added slowly a solution of (2R)-2-({N-benzoxy-amino}methyl)-7-octenoic acid (358 mg, 1.29 mmol) in dichloromethane (10 mL). The mixture was stirred at 0° C. for 3 hours. The volatiles were removed by evaporation under vacuum. Dichloromethane (20 mL) was added to it. It was washed with brine (20 mL×2), and dried over MgSO4. Filtration and evaporation under vacuum provided the title compound. MH+306.
Workup
- stirringThe mixture was stirred at 0° C. for 3 hours
- customThe volatiles were removed by evaporation under vacuum
- additionDichloromethane (20 mL) was added to it
- washIt was washed with brine (20 mL×2)
- dry with materialdried over MgSO4
- filtrationFiltration and evaporation under vacuum
Sources & evidence
- ORD record
- ord-bb2911321b244392b96e0bffada4221d
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07507726B2
Reaction notes
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