Hydrochloric Acid → HCID 7068523, compound

HRID 1663198Notes

Reaction equation

HRID 1663198 reaction equation
[N:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=O)=[C:2]=[O:3].Cl.[NH2:15][C@H:16]([C:21]([O:23]C)=[O:22])[CH2:17][CH:18]([CH3:20])[CH3:19].[OH-].[Na+].Cl>CCN(CC)CC>[O:3]=[C:2]1[N:15]([C@@H:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:21]([OH:23])=[O:22])[C:6](=[O:8])[C:5]2[C:4](=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:1]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 519494Methyl 2-isocyanatobenzoateHCID 2723695Leucine methyl ester hydrochloride

Product 1

HCID 7068523HCID 7068523, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

Refer to Scheme 1, a mixture of methyl 2-isocyanatobenzoate (0.5 g, 2.82 mmol) and (S)-methyl leucinate HCl (0.52 g, 2.82 mmol) salt and 1 mL of Et3N was heated to 80° C. for 2 hours. 2 mL of 2M NaOH aqueous solution was added to above mixture and then heated to 100° C. overnight. The mixture was neutralized with concentrated HCl. Extracted by EtOAc and dried over MgSO4. Removing solvent gave the crude product, which used for next step without further purification. [M+H] calc'd for C14H16N2O4, 277; found, 277.

Workup

  1. temperatureheated to 100° C. overnight
  2. extractionExtracted by EtOAc
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-608b1df86d154742bc3b15bfc37ca1aa
Source dataset
uspto-grants-2011_10
Patent number
US08034822B2

Reaction notes

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