Hydrochloric Acid → HCID 58959882, compound

HRID 915889Notes

Reaction equation

HRID 915889 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.C1C=CC2N(O)N=NC=2C=1.[OH:25][CH2:26][C:27](O)=[O:28].Cl>C(Cl)Cl.C(N(CC)CC)C>[OH:28][CH2:27][C:26]([N:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]1)=[O:25]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 757Glycolic AcidHCID 757711-HydroxybenzotriazoleHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 58959882HCID 58959882, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3.0 g of tert-butyl piperidin-4-ylcarbamate in 60 ml of methylene chloride, were added 2.5 ml of triethylamine, 2.4 g of HOBt, 1.3 g of hydroxyacetic acid and 3.5 g of WSCD hydrochloride, and the reaction mixture was stirred at room temperature for 18 hours. 1 M hydrochloric acid was added to the reaction mixture, and this was extracted with EtOAc. The organic layer was washed with aqueous saturated sodium hydrogencarbonate solution, water and brine. This was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified with silica gel column chromatography (eluent: chloroform/MeOH=50/1) to obtain 2.8 g of tert-butyl [1-(hydroxyacetyl)piperidin-4-yl]carbamate.

Workup

  1. extractionthis was extracted with EtOAc
  2. washThe organic layer was washed with aqueous saturated sodium hydrogencarbonate solution, water and brine
  3. dry with materialThis was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe resulting residue was purified with silica gel column chromatography (eluent: chloroform/MeOH=50/1)

Sources & evidence

ORD record
ord-a3f3d80090ad439f9c05a5784a58d055
Source dataset
uspto-grants-2007_09
Patent number
US07268150B2

Reaction notes

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