Hydrochloric Acid → 11-(((Benzyloxy)carbonyl)amino)undecanoic acid
Reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[C:15](Cl)([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].Cl>[OH-].[Na+]>[C:15]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
In a 2 N-aqueous solution of sodium hydroxide (500 ml) was dissolved 11-aminoundecanoic acid (30.2 g, 0.15 mol) under mild heating (50° C.). With intense stirring, carbobenzoxy chloride (30.7 g, 0.18 mol) was added in 4 installments over a period of 30 minutes, after which the mixture was stirred for 2 hours. The reaction mixture was cooled with ice, adjusted to pH 2 with 6 N-hydrochloric acid and extracted with ethyl acetate (600 ml). The ethyl acetate layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off and petroleum ether was added to the crystalline residue. After cooling, the crystals were recovered by filtration. By the above procedure there was obtained 36.0 g of N-carbobenzoxy-11-aminoundecanoic acid. m.p. 96°-97° C.; Rf1 =0.67.
Workup
- temperatureThe reaction mixture was cooled with ice
- extractionextracted with ethyl acetate (600 ml)
- washThe ethyl acetate layer was washed with water
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was distilled off
- additionpetroleum ether was added to the crystalline residue
- temperatureAfter cooling
- filtrationthe crystals were recovered by filtration
Sources & evidence
- ORD record
- ord-0f1e5327a2b643bfa549df8236a9eb0a
- Source dataset
- uspto-grants-1984_02
- Patent number
- US04430265
Reaction notes
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