Hydrochloric Acid → (3R,4S,5S)-3-Amino-5-(3,5-difluoro-4-nitro-benzyl)-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-4-ol hydrochloride

HRID 420305Notes

Reaction equation

HRID 420305 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]([F:22])[C:19]([N+:23]([O-:25])=[O:24])=[C:18]([F:26])[CH:17]=2)[CH2:11][S:10](=[O:28])(=[O:27])[CH2:9]1)(C)(C)C.[ClH:30]>O1CCOCC1>[ClH:30].[NH2:7][C@@H:8]1[C@@H:13]([OH:14])[C@H:12]([CH2:15][C:16]2[CH:17]=[C:18]([F:26])[C:19]([N+:23]([O-:25])=[O:24])=[C:20]([F:22])[CH:21]=2)[CH2:11][S:10](=[O:27])(=[O:28])[CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131729378[(3R*,4S*,5S*)-5-(3,5-Difluoro-4-nitro-benzyl)-4-hydroxy-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-3-yl]-carbamic acid tert-butyl ester

Product 1

HCID 131729379(3R,4S,5S)-3-Amino-5-(3,5-difluoro-4-nitro-benzyl)-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-4-ol hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

To [(3R,4S,5S)-5-(3,5-difluoro-4-nitro-benzyl)-4-hydroxy-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-3-yl]-carbamic acid tert-butyl ester (0.873 g, 2 mmol) was added 4N HCl in dioxane (5 mL) and the reaction mixture was stirred for 3 h at 40° C. After evaporation the residue was stirred with Et2O, filtered and dried to provide the title compound as a beige solid: TLC (CH2Cl2-MeOH-AcOH-H2O 180:20:2:1) Rf=0.13; HPLC RtA=1.22 min; ESIMS [M+H]+=337; 1H NMR (600 MHz, DMSO-d6): δ 8.34 (s, 3H), 7.37 (d, 2H), 6.14 (d, 1H), 3.3-3.5 (m, 4H), 3.31 (d, 1H), 3.22 (d, 1H), 3.12 (m, 1H), 2.74 (dd, 1H), 2.26 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-e3e361ab2ac94f2aac3cd7a09d4951cf
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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