Hydrochloric Acid → HCID 178462368, compound

HRID 887355Notes

Reaction equation

HRID 887355 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-551970c74f6b45b28bb19d71fe7ee202
Source dataset
uspto-grants-2012_08
Patent number
US08247421B2

Reaction notes

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