Hydrochloric Acid → 2-(S)-(benzooxazol-2-ylamino)-3-cyclohexyl propionic acid

HRID 969785Notes

Reaction equation

HRID 969785 reaction equation
[CH2:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C@H:8]([NH2:12])[C:9]([OH:11])=[O:10])[CH2:3][CH2:2]1.[OH-].[Na+].Cl[C:16]1[O:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1.Cl>CS(C)=O>[O:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[NH:12][C@@H:8]([CH2:7][CH:4]1[CH2:3][CH2:2][CH2:1][CH2:6][CH2:5]1)[C:9]([OH:11])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 119862-ChlorobenzoxazoleHCID 14798Sodium HydroxideHCID 7124213-Cyclohexyl-L-alanine

Product 1

HCID 210822522-(S)-(benzooxazol-2-ylamino)-3-cyclohexyl propionic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A slurry of L-cyclohexylalanine (2.44 g, 14.3 mmol) and powdered NaOH (1.14 g, 28.6 mmol) in DMSO (20 mL) was heated to 100° C. for 20 min until the mixture viscosity decreased and stirring was enabled. 2-Chlorobenzoxazole (1.99 g, 13.0 mmol) was added, and the solution was stirred at 100° C. for 4 h. Upon cooling to room temperature, the solution was poured into 1 M HCl. The precipitate was filtered and dried to afford 2-(S)-(benzooxazol-2-ylamino)-3-cyclohexyl propionic acid was isolated as a white powder (1.69 g, 41%).

Workup

  1. stirringthe solution was stirred at 100° C. for 4 h
  2. filtrationThe precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-eef66121ebb64ef787feda12fbd56dd8
Source dataset
uspto-grants-2007_12
Patent number
US07307095B2

Reaction notes

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