Triethylamine → HCID 131736930, compound

HRID 56428Notes

Reaction equation

HRID 56428 reaction equation
[NH2:1][CH:2]1[CH:7]([OH:8])[CH2:6][CH2:5][CH:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:3]1.C(N(CC)CC)C.[CH2:21]([O:28][C:29](ON1C(=O)CCC1=O)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCl>[CH2:21]([O:28][C:29]([NH:1][CH:2]1[CH:7]([OH:8])[CH2:6][CH2:5][CH:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:3]1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 69078398Ethyl 3-amino-4-hydroxycyclohexanecarboxylate

Product 1

HCID 131736930HCID 131736930, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of Racemate-ethyl 3-amino-4-hydroxycyclohexanecarboxylate (4.7 g, 25 mmol) in 120 mL of dichloromethane was added triethylamine (3.03 g, 30 mmol), followed by the addition of N-(benzyloxycarbonyloxy)succinimide (6.55 g, 26.3 mmol) at 0° C. The reaction mixture was stirred at room temperature for 16 hours and then diluted with 200 mL of dichloromethane. The solution was washed with 5% citric acid solution (2×150 mL), 5% potassium carbonate solution (2×150 mL) and brine (200 mL). The organic layer was separated, dried over anhydrous sodium sulfate and filtered, followed by concentration under reduced pressure. The resultant oily matter was purified by silica gel chromatography (ethyl acetate:petroleum ether=1:4˜2:5), to thereby give the title compound (7.0 g, 87%) as a yellow oil. MS (ES+) C17H23NO5 requires: 321, found: 322 [M+H]+.

Workup

  1. washThe solution was washed with 5% citric acid solution (2×150 mL), 5% potassium carbonate solution (2×150 mL) and brine (200 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationfollowed by concentration under reduced pressure
  6. customThe resultant oily matter was purified by silica gel chromatography (ethyl acetate:petroleum ether=1:4˜2:5)

Sources & evidence

ORD record
ord-95cacedc8d0d4470905019ff4fdfad61
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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