Hydrochloric Acid → HCID 69507503, compound

HRID 2181749Notes

Reaction equation

HRID 2181749 reaction equation
FC(F)(F)S([O:6][Si:7]([CH2:12][CH3:13])([CH2:10][CH3:11])[CH2:8][CH3:9])(=O)=O.O[C@H:17]([C:21]([CH3:38])=[CH:22][C:23]1[N:24]=[C:25]([CH2:28][O:29][C:30]([O:32][CH2:33][C:34]([Cl:37])([Cl:36])[Cl:35])=[O:31])[S:26][CH:27]=1)[CH2:18][CH:19]=[CH2:20].N1C(C)=CC=CC=1C.Cl>C(Cl)Cl>[CH2:12]([Si:7]([CH2:8][CH3:9])([CH2:10][CH3:11])[O:6][C@H:17]([C:21]([CH3:38])=[CH:22][C:23]1[N:24]=[C:25]([CH2:28][O:29][C:30]([O:32][CH2:33][C:34]([Cl:36])([Cl:37])[Cl:35])=[O:31])[S:26][CH:27]=1)[CH2:18][CH:19]=[CH2:20])[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79372,6-LutidineHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 69507241HCID 69507241, compound

Product 1

HCID 69507503HCID 69507503, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylsilyl trifluromethanesulfonate (15 mL) is added dropwise to a −78° C. solution of (4S)-4-hydroxy-5-methyl-6-(2-(2,2,2-trichloroethoxycarbonyloxymethyl)-thiazol-4-yl)-1,5-hexadiene (7.65 g) and 2,6-lutidine (10 mL) in 50 mL of CH2Cl2. After the addition, the reaction mixture is allowed to warm to ambient temperature and is stirred for 5 hours. The reaction mixture is poured into 2 N HCl and extracted with ether. The combined organic layers were washed with 10% aq NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated. Flash chromatography on SiO2 (hexanes/ethyl acetate, 20:1) provides the product as a colorless oil (9.39 g).

Workup

  1. additionAfter the addition
  2. extractionextracted with ether
  3. washThe combined organic layers were washed with 10% aq NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c3979f5f794f410bb1c6c52b4ad38e14
Source dataset
uspto-grants-2005_05
Patent number
US06893859B2

Reaction notes

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