Triethylamine → 1-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acid

HRID 968337Notes

Reaction equation

HRID 968337 reaction equation
N[C@H]1C[CH2:5][CH2:4][C@@H:3]1[C:7]([OH:9])=[O:8].C([N:12](CC)CC)C.[C:17]([O:21][C:22]([O:24]C(OC(C)(C)C)=O)=O)([CH3:20])([CH3:19])[CH3:18]>CO>[CH3:18][C:17]([O:21][C:22]([NH:12][C:3]1([C:7]([OH:9])=[O:8])[CH2:4][CH2:5]1)=[O:24])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 10997062(1S,2S)-2-AMINOCYCLOPENTANECARBOXYLIC ACID

Product 1

HCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1S,2S)-2-Amino-cyclopentanecarboxylic acid (NH2-ACPC-OH, JKMI91, 5.18 g, 40.1 mmol) (See LePlae, Umezawa, Lee & Gellman (2001) J. Org. Chem. 66:5629-5632) was dissolved in methanol (409 mL). Triethylamine (11.16 mL, 80.2 mmol) was added via syringe followed by di-tert-butyl-dicarbonate (8.74 g, 40.1 mmol). The reaction mixture was stirred at room temperature for 2 h. The solvent was removed by rotary evaporation. The residue was diluted with ethyl acetate (250 mL), washed with 0.5 M NaHSO4 (1×100), and saturated aqueous NaCl solution (1×100). The organic layer was dried over MgSO4, filtered, and concentrated to give a white solid. The crude product was purified by column chromatography (7:3:0.3) hexane:ethyl acetate:acetic acid). Acetic acid was removed on the high-vacuum rotary evaporator. Benzene (2×100 mL) was added and removed on the rotary evaporator. The residue was dried under high vacuum overnight to give a white solid (Boc-ACPC-OH, JKMI103, 7.65 g, 83%). 1H NMR (250 MHz, CDCl3): δ=11.22 (br. s, 1H), 4.93 (br. s, 1H), 4.02 (br. s, 1H), 2.69 (br. s, 1H), 2.14-1.89 (m, 3H), 1.68 (quin., J=6.7 Hz, 2H), 1.51-1.35 (m, 10H) ppm.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. additionThe residue was diluted with ethyl acetate (250 mL)
  3. washwashed with 0.5 M NaHSO4 (1×100), and saturated aqueous NaCl solution (1×100)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a white solid
  8. customThe crude product was purified by column chromatography (7:3:0.3) hexane
  9. customAcetic acid was removed on the high-vacuum rotary evaporator
  10. additionBenzene (2×100 mL) was added
  11. customremoved on the rotary evaporator
  12. customThe residue was dried under high vacuum overnight

Sources & evidence

ORD record
ord-256b961d978646d4b7b12fd2998c3d18
Source dataset
uspto-grants-2005_10
Patent number
US06958384B2

Reaction notes

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