Trifluoroacetic acid → HCID 10224154, compound

HRID 1835494Notes

Reaction equation

HRID 1835494 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([C@@H:17]1[CH2:22][CH2:21][CH2:20][CH2:19][N:18]1[C:23](=[O:36])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:16])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([C@@H:17]1[CH2:22][CH2:21][CH2:20][CH2:19][N:18]1[C:23](=[O:36])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15479956HCID 15479956, compound

Product 1

HCID 10224154HCID 10224154, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-(6-{[1-(1-tridecanoyl-piperidin-2-yl)-methanoyl]-amino}-hexyl)-carbamic acid tert-butyl ester (3.9 g, 7.45 mmol) in DCM (40 mL) was treated with TFA (8 mL) at −20° C. for two days until disappearance of the starting material. The reaction mixture was allowed to warm up to rt and was washed with an aqueous saturated solution of K2CO3. Extraction, drying over MgSO4 and evaporation in vacuo gave a yellow oil. Purification via flash chromatography (SiO2, 5×13 cm2 column) using a mixture (90:10:2) of DCM:MeOH(5% aqueous solution of NH3) gave the title compound (1.35 g) as a pale yellow oil. The residue was taken in anhydrous DCM (25 mL) and treated with TFA (246 μL, 365 mg) at —10° C. Evaporation of the solvents gave the title compound (1.67 g, 3.11 mmol) as a yellow oil in a 42% yield.

Workup

  1. washwas washed with an aqueous saturated solution of K2CO3
  2. extractionExtraction
  3. dry with materialdrying over MgSO4 and evaporation in vacuo
  4. customgave a yellow oil
  5. customPurification via flash chromatography (SiO2, 5×13 cm2 column)

Sources & evidence

ORD record
ord-24df8e6985164031b5f10248f759cf8e
Source dataset
uspto-grants-2004_08
Patent number
US06770656B2

Reaction notes

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