Hydrochloric Acid → HCID 9855841, compound

HRID 1060262Notes

Reaction equation

HRID 1060262 reaction equation
[CH2:1]([C@H:4]([CH2:8][C:9]#[C:10][CH3:11])[C:5]([OH:7])=O)[CH2:2][CH3:3].C(Cl)(=O)C(Cl)=O.Cl.[NH2:19][CH2:20][C:21]([NH2:23])=[O:22].Cl>ClCCl.CN(C)C=O.O.C(N(CC)CC)C>[NH2:23][C:21](=[O:22])[CH2:20][NH:19][C:5](=[O:7])[C@H:4]([CH2:1][CH2:2][CH3:3])[CH2:8][C:9]#[C:10][CH3:11]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 2723639Glycinamide hydrochlorideHCID 9793877(2R)-2-Propyl-4-hexynoic acid

Product 1

HCID 9855841HCID 9855841, compoundYield 70%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

(2R)-2-Propyl-4-hexynoic acid (2.0 g, 13 mmol, prepared according to U.S. Pat. No. 5,786,380) in dichloromethane (20 mL) was treated with 2 drops of N,N-dimethylformamide and freshly distilled oxalyl chloride (1.25 equivalents) at 0° C. The mixture was allowed to warm to ambient temperature. After stirring for 3 hours at ambient temperature, the solvents were removed under reduced pressure to provide crude acid chloride. The crude acid chloride was dissolved in dichloromethane (15 mL) and added dropwise to a solution of 2-aminoacetamide hydrochloride (14 mmol) and triethylamine (3.5 mL) in water at 0° C. The mixture was allowed to warm to ambient temperature. After stirring for 3 hours at ambient temperature, the mixture was cooled to about 5° C. and treated with 1N HCl until pH=2. The resulting white solid was collected by filtration, dried and recrystallized from ethyl acetate to provide the title compound (70% yield).

Workup

  1. customthe solvents were removed under reduced pressure
  2. customto provide crude acid chloride
  3. temperatureto warm to ambient temperature
  4. stirringAfter stirring for 3 hours at ambient temperature
  5. temperaturethe mixture was cooled to about 5° C.
  6. filtrationThe resulting white solid was collected by filtration
  7. customdried
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-55b3c4304a2d4747ba6092b4895c5f8f
Source dataset
uspto-grants-2003_02
Patent number
US06521790B2

Reaction notes

Loading…