Hydrochloric Acid → HCID 178462368, compound

HRID 1853479Notes

Reaction equation

HRID 1853479 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-ca3d3467848e4ac19696b9f280953c39
Source dataset
uspto-grants-2015_02
Patent number
US08962642B2

Reaction notes

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