Ethyl Acetate → HCID 13629136, compound

HRID 464240Notes

Reaction equation

HRID 464240 reaction equation
Br[CH2:2][C:3]([OH:19])([C:15]([F:18])([F:17])[F:16])[CH:4]([NH:12][CH:13]=[S:14])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CC(C)=O>[OH:19][C@:3]1([C:15]([F:18])([F:17])[F:16])[CH2:2][S:14][CH:13]=[N:12][C@@H:4]1[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 20221472HCID 20221472, compound

Product 1

HCID 13629136HCID 13629136, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3.67 gms of (2R,3S) and 2S,3R)-t-butyl 4-bromo-3-hydroxy-2-thioformamido-3-trifluoromethylbutyrate in 65 ml acetone was added 4.15 g powdered anhydrous potassium carbonate. The reaction mixture was stirred for 30 minutes at room temperature, filtered and evaporated to dryness under reduced pressure. The crude brown oil was then purified by chromatography on silica gel using 80:20 hexane:ethyl acetate as the eluting solvent to give 0.781 gms of white solid, (4R,5S) and (4S,5R)-t-butyl 5-hydroxy-5-trifluoromethyl-4,5-dihydro-6H-1,3-thiazine-4-carboxylate (yield 27%) m.p. 126.5°-127.5° C. NMR (CDCL3): δ=1.55 (s, 9H), 2.93, 3.13 (AB-q, J=13.8 Hz, 2H), 4.13 (d, J=2.7 Hz, 1H), 5.33 (s, 1H), 8.25 (d-d, J=2.7, 1.2 Hz, 1H).

Workup

  1. filtrationfiltered
  2. customevaporated to dryness under reduced pressure
  3. customThe crude brown oil was then purified by chromatography on silica gel using 80:20 hexane

Sources & evidence

ORD record
ord-b00309aad51347e2bf65bea85a1e7fb1
Source dataset
uspto-grants-1985_10
Patent number
US04547371

Reaction notes

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