Hydrochloric Acid → HCID 178462368, compound

HRID 40853Notes

Reaction equation

HRID 40853 reaction equation
[OH:1][C@H:2]([CH3:22])[C:3]([NH:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C@H:12]([NH:14]C(=O)OC(C)(C)C)[CH3:13])[CH2:8][CH2:7]1)=[O:4].Cl.O1CCOCC1>ClCCl>[NH2:14][C@@H:12]([C@H:9]1[CH2:8][CH2:7][C@H:6]([NH:5][C:3](=[O:4])[C@H:2]([OH:1])[CH3:22])[CH2:11][CH2:10]1)[CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178462369HCID 178462369, compound

Product 1

HCID 178462368HCID 178462368, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trans-tert-butyl (R)-1-(4-((R)-2-hydroxypropanamido)cyclohexyl)ethylcarbamate (66 mg, 0.21 mmol) was dissolved in dichloromethane (10 mL). A solution of HCl in dioxane (209.9 μL of 4 M, 0.84 mmol) was added. The reaction mixture was stirred at ambient temperature for 18 hours. The crude mixture was concentrated in vacuo and coevaporated three times with diethylether. The residue was dissolved in methanol (10 mL), passed through a sodium bicarbonate cartridge and concentrated in vacuo to give the desired compound as a white solid (45 mg, quantitative yield).

Workup

  1. concentrationThe crude mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in methanol (10 mL)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3aa0d4c33127483da5b970f1775ca0fb
Source dataset
uspto-grants-2013_09
Patent number
US08530489B2

Reaction notes

Loading…