Triethylamine → HCID 178497926, compound
Reaction equation
C(OC([NH:8][C@@H:9]1[CH2:14][CH2:13][C@H:12](C(O)=O)[CH2:11][CH2:10]1)=O)(C)(C)C.C(N(CC)CC)C.ClC(OCC)=O.[NH2:31][C:32]1[C:41]([NH2:42])=[CH:40][CH:39]=[CH:38][C:33]=1[C:34]([O:36][CH3:37])=[O:35].C(=O)(O)[O-].[Na+]>O1CCCC1>[NH2:31][C:32]1[C:41]([NH:42][C@H:12]2[CH2:13][CH2:14][C@@H:9]([NH2:8])[CH2:10][CH2:11]2)=[CH:40][CH:39]=[CH:38][C:33]=1[C:34]([O:36][CH3:37])=[O:35]Participants
Conditions
- Temperature
- 0 °C
Procedure
2.4 g (9.9 mmol) of cis-4-(tert-butoxycarbonylamino)-cyclohexanecarboxylic acid and 2.7 ml (19.7 mmol) of triethylamine were dissolved in 70 ml of anhydrous tetrahydrofuran and, at −10° C., a solution of 0.94 ml (9.9 mmol) of ethyl chloroformate in 25 ml of anhydrous tetrahydrofuran was added dropwise. The mixture was then stirred at 0° C. for 1 hour. After this, 1.6 g (9.9 mmol) of methyl 2,3-diaminobenzoate were added, and the mixture was stirred at room temperature for 16 hours. The reaction mixture was poured into ice-water and made alkaline with aqueous sodium bicarbonate solution. This aqueous phase was extracted with ethyl acetate. The organic phase was then washed with aqueous sodium bicarbonate solution and water, dried and concentrated in vacuo. 2.7 g of the product were obtained.
Workup
- stirringthe mixture was stirred at room temperature for 16 hours
- extractionThis aqueous phase was extracted with ethyl acetate
- washThe organic phase was then washed with aqueous sodium bicarbonate solution and water
- customdried
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-478b2d46d02b444a8a3119b1c818caf9
- Source dataset
- uspto-grants-2004_05
- Patent number
- US06737421B1
Reaction notes
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