Formic Acid → HCID 59570976, compound

HRID 2192934Notes

Reaction equation

HRID 2192934 reaction equation
[C:1]([O:4][CH2:5][C:6]([C:9]1[N:10]=[C:11]([NH:14]C(OCC=C)=O)[S:12][CH:13]=1)([OH:8])[CH3:7])(=[O:3])[CH3:2].C(N)CCC.C(O)=O.Cl>C1COCC1>[C:1]([O:4][CH2:5][C:6]([C:9]1[N:10]=[C:11]([NH2:14])[S:12][CH:13]=1)([OH:8])[CH3:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 8007ButylamineHCID 59570885HCID 59570885, compound

Product 1

HCID 59570976HCID 59570976, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-{[(allyloxy)carbonyl]amino}-1,3-thiazol-4-yl)-2-hydroxypropyl acetate (790 mg) in THF (10 mL) were added n-butylamine (0.52 mL), formic acid (0.20 mL), and tetrakistriphenylphosphine palladium (33 mg) at room temperature, followed by stirring at room temperature for 30 minutes. To the reaction mixture was added 1 M hydrochloric acid (30 mL) at room temperature, followed by extraction with ethyl acetate. The aqueous layer was adjusted to pH 9 using saturated aqueous sodium bicarbonate, followed by extraction with a solvent (ethyl acetate:isopropyl alcohol=3:1, 100 mL×3). The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. After concentration, 2-(2-amino-1,3-thiazol-4-yl)-2-hydroxypropyl acetate (261 mg) was obtained as a pale yellow oily substance. The obtained pale yellow oily substance was subjected to optical resolution with chiral column chromatography (Product Name: Chiralcel OJ-H, hexane:ethanol:diethylamine=30:70:0.1) to obtain optical active products of 2-(2-amino-1,3-thiazol-4-yl)-2-hydroxypropyl acetate at a first peak and a second peak in yields of 37% and 25%, respectively (>95% ee) (absolute arrangement was not determined).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. extractionfollowed by extraction with a solvent (ethyl acetate:isopropyl alcohol=3:1, 100 mL×3)
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationAfter concentration

Sources & evidence

ORD record
ord-9a4d2fd838fc4043924032b40a8244ac
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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