Hydrochloric Acid → HCID 45256133, compound

HRID 1809430Notes

Reaction equation

HRID 1809430 reaction equation
Cl.[CH3:2][C:3]([C:13]1[CH:17]=[C:16]([NH:18][C:19](=[O:32])[C:20]([CH3:31])([S:22]([CH:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)(=[O:24])=[O:23])[CH3:21])[O:15][N:14]=1)([CH3:12])[CH2:4][O:5]C1CCCCO1>C(O)C>[OH:5][CH2:4][C:3]([C:13]1[CH:17]=[C:16]([NH:18][C:19](=[O:32])[C:20]([CH3:31])([S:22]([CH:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)(=[O:24])=[O:23])[CH3:21])[O:15][N:14]=1)([CH3:12])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 45111496HCID 45111496, compound

Product 1

HCID 45256133HCID 45256133, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
54 °C

Procedure

2120 mL 10M HCl in ethanol is added to a mixture of 10.8 kg N-{3-[1,1-Dimethyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-isoxazol-5-yl}-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionamide in 65 L ethanol at 51° C. The mixture is stirred for 2.5 h at 54° C. and then is cooled to 1° C. The suspension is filtered and the filter cake is washed once with 5 L cold ethanol and once with 7 L ethanol. Drying of the filter cake provides 8001 g product. ES-MS: m/z 375 [M+H];]; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.19 (6H, s) 1.59-1.72 (2H, m), 1.68 (6H, s), 1.80-1.86 (2H, m), 3.34-3.43 (4H, m), 3.85-3.94 (3H, m), 4.80 (1H, t, 3JH,H=5.5 Hz), 6.30 (1H, s), 11.27 (1H, s).

Workup

  1. temperatureis cooled to 1° C
  2. filtrationThe suspension is filtered
  3. washthe filter cake is washed once with 5 L cold ethanol and once with 7 L ethanol
  4. customDrying of the filter cake

Sources & evidence

ORD record
ord-967d29f8fce3410aaafb6d7252169e7a
Source dataset
uspto-grants-2013_01
Patent number
US08362039B2

Reaction notes

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