Hydrochloric Acid → HCID 131729388, compound

HRID 420314Notes

Reaction equation

HRID 420314 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[C@@H:13]([OH:14])[C@H:12]([CH2:15][C:16]2[CH:21]=[C:20]([O:22][CH:23]([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])[C:19]([N+:32]([O-:34])=[O:33])=[C:18]([F:35])[CH:17]=2)[CH2:11][S:10](=[O:37])(=[O:36])[CH2:9]1)(C)(C)C.[ClH:39]>C1COCC1.O1CCOCC1>[ClH:39].[NH2:7][C@@H:8]1[C@@H:13]([OH:14])[C@H:12]([CH2:15][C:16]2[CH:21]=[C:20]([O:22][CH:23]([C:24]([F:27])([F:26])[F:25])[C:28]([F:31])([F:29])[F:30])[C:19]([N+:32]([O-:34])=[O:33])=[C:18]([F:35])[CH:17]=2)[CH2:11][S:10](=[O:36])(=[O:37])[CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131729387HCID 131729387, compound

Product 1

HCID 131729388HCID 131729388, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of {(3R,4S,5S)-5-[3-fluoro-4-nitro-5-(2,2,2-trifluoro-1-trifluoromethyl-ethoxy)-benzyl]-4-hydroxy-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-3-yl}-carbamic acid tert-butyl ester (3.42 g, 5.85 mmol) in THF (5 mL) was added 4N HCl in dioxane (20 mL) and the reaction mixture was stirred for 2 h at 25° C. After evaporation the residue was stirred with Et2O, filtered and dried to provide the title compound as a beige solid: TLC (EtOAc-MeOH 9:1) Rf=0.12; HPLC RtA=1.76 min; ESIMS [M+H]+=485; 1H NMR (400 MHz, CD3OD): δ 7.24 (s, 1H), 7.18 (d, 1H), 6.29 (m, 1H), 3.3-3.7 (m, 5H), 3.21 (dd, 1H), 2.97 (m, 1H), 2.70 (dd, 1H), 2.42 (m, 1H).

Workup

  1. customAfter evaporation the residue
  2. stirringwas stirred with Et2O
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-27b42ff8ee6249eebff571ca1e98716c
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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