cyclopentyl (2S)-[(tert-butoxycarbonyl)amino](cyclohexyl)acetate → (S)-Amino-cyclohexyl-acetic acid cyclopentyl ester

HRID 548214Notes

Reaction equation

HRID 548214 reaction equation
[CH:1]1([O:6][C:7](=[O:23])[C@@H:8]([NH:15]C(OC(C)(C)C)=O)[CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)(C(F)(F)F)=O.C(Cl)Cl.C(Cl)Cl>[CH:1]1([O:6][C:7](=[O:23])[C@@H:8]([NH2:15])[CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 57658394cyclopentyl (2S)-[(tert-butoxycarbonyl)amino](cyclohexyl)acetate

Product 1

HCID 57658319(S)-Amino-cyclohexyl-acetic acid cyclopentyl esterYield 96.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

(S)-tert-butoxycarbonylamino-cyclohexyl-acetic acid cyclopentyl ester (1.17 g, 3.60 mmol) was dissolved in a TFA/DCM mixture (1:1, 10 ml) at 0° C. The solution was stirred for 90 minutes, the solvent removed in vacuo. The residue was azetroped with a DCM/heptane mixture (2×) to give a gum. The gum was redissolved in DCM (10 ml) and washed with saturated aqueous NaHCO3 solution (3×10 ml), dried (MgSO4) and filtered. The solvent of the filtrate was removed in vacuo to give the product as an oil (0.780 g, 78% yield). 1H NMR (300 MHz, CDCl3), δ: 1.00-1.40 (10H, m, CH×10), 1.50-2.00 (8H, m, CH×8), 3.25 (1H, d, CH, J=7.2 Hz), 5.20 (1H, m, CH).

Workup

  1. customthe solvent removed in vacuo
  2. customto give a gum
  3. washwashed with saturated aqueous NaHCO3 solution (3×10 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe solvent of the filtrate was removed in vacuo

Sources & evidence

ORD record
ord-486524f6c65a4121ba7927aace829af7
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

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