Hydrochloric Acid → HCID 117740973, compound

HRID 1775881Notes

Reaction equation

HRID 1775881 reaction equation
[ClH:1].[NH2:2][CH:3]([C:7]1[N:8]=[C:9]([CH3:13])[O:10][C:11]=1[CH3:12])[C:4]([OH:6])=[O:5].Cl.[CH3:15]O>>[ClH:1].[NH2:2][CH:3]([C:7]1[N:8]=[C:9]([CH3:13])[O:10][C:11]=1[CH3:12])[C:4]([O:6][CH3:15])=[O:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 117740728HCID 117740728, compound

Product 1

HCID 117740973HCID 117740973, compoundYield 84%

Procedure

Prepared using General Procedure 22: To a stirred solution of 2-amino-2-(2,5-dimethyloxazol-4-yl)acetic acid hydrochloride (150 mg, 0.726 mmol) in MeOH (5 mL) was added HCl (1.2 mL of a 37% aqueous solution, 14.5 mmol) and the mixture heated under reflux for 4 h. The mixture was allowed to cool and solvents evaporated. The residue was treated with MeOH (12 mL) and filtered. The filtrate was evaporated to afford 135 mg (84%) of methyl 2-amino-2-(2,5-dimethyloxazol-4-yl)acetate hydrochloride INT-43. LCMS-ESI (m/z) calculated for C8H12N2O3: 184.1. found 185.1 [M+H]+, tR=0.23 min (Method 11). 1H NMR (400 MHz, DMSO) δ 8.94 (br s, 3H), 5.35 (s, 1H), 3.73 (s, 3H), 2.38 (s, 3H), 2.36 (s, 3H).

Workup

  1. customPrepared
  2. temperatureheated
  3. temperatureunder reflux for 4 h
  4. temperatureto cool
  5. customsolvents evaporated
  6. additionThe residue was treated with MeOH (12 mL)
  7. filtrationfiltered
  8. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-b3f6063ce70549fd9861a5d605cda177
Source dataset
uspto-grants-2016_02
Patent number
US09260427B2

Reaction notes

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