L-Homoserine → HCID 71183365, compound

HRID 717063Notes

Reaction equation

HRID 717063 reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)=[CH:11][C:6]=2[C:5](=O)[O:4][C:3]1=[O:24].[NH2:25][C@H:26](C(O)=O)[CH2:27][CH2:28][OH:29]>C(O)(=O)C>[OH:29][CH2:28][CH2:27][C@H:26]1[C:3](=[O:24])[N:2]([CH3:1])[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:20])[F:21])=[CH:14][CH:13]=3)=[CH:11][C:6]=2[C:5](=[O:4])[NH:25]1

Participants

4

Reactant 2

HCID 12647L-HomoserineHCID 71183343HCID 71183343, compound

Product 1

HCID 71183365HCID 71183365, compoundYield 10.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

1-Methyl-6-(4-(trifluoromethoxy)phenyl)-1H-benzo[d][1,3]oxazine-2,4-dione (60 mg, 0.178 mmol) and L-homoserine (23.3 mg, 0.196 mmol, 1.1 equiv.) were added to a magnetically stirred 0.5-2 mL Smith process vial containing 0.75 mL glacial acetic acid. Reaction mixture was then heated for 2 hours at 130° C. Excess acetic acid was then removed en vacuo, residue was dissolved into a minimal amount of acetonitrile and purified by reverse-phase preparative HPLC to give the title compound (7.6 mg) following removal of solvent as a clear yellow film.

Workup

  1. customReaction mixture
  2. customExcess acetic acid was then removed en vacuo, residue
  3. dissolutionwas dissolved into a minimal amount of acetonitrile
  4. custompurified by reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-326b95aa29d64866b0bcbff72c41ad3d
Source dataset
uspto-grants-2015_11
Patent number
US09193694B2

Reaction notes

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