1-{[(benzyloxy)carbonyl]amino}cyclohexanecarboxylic acid synthesis
- Product Name:1-{[(benzyloxy)carbonyl]amino}cyclohexanecarboxylic acid
- CAS Number:17191-43-4
- Molecular formula:C15H19NO4
- Molecular Weight:277.32
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Yield: 89%
Reaction Conditions:
with sodium hydroxide in water for 2 h;
Steps:
B1a.1 Step 1
To a solution of l-aminocyclohexane-1-carboxylic acid (10.0 g, 70.0 mmol) in a 1M NaOH solution (100 mL) was added benzyl chloroformate (12.0 ml, 84.0 mmol). The reaction mixture was stirred for 2 h while maintaining pH 9 by addition of a 1M NaOH solution as necessary. The resulting solution was washed with Et2O (2×100 mL), then the aqueous layer was adjusted to pH 0 with a conc. HCl solution and the solution was extracted with EtOAc (3×150 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to yield 1-(benzyloxycarbonylamino)cyclohexane-1-carboxylic acid (17.3 g, 89%): TLC (25% EtOAc/hex) Rf0.07
References:
Bayer Corporation US6353006, 2002, B1 Location in patent:Page column 29
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