Potassium Carbonate → HCID 44625098, compound

HRID 420273Notes

Reaction equation

HRID 420273 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:41]=[CH:42][CH:43]=1)[CH2:8][N:9]1[C@@H:17]2[C@H:12]([C@H:13]([CH2:20][C:21]3[CH:26]=[C:25]([CH2:27][C@H:28]([OH:33])[C:29]([F:32])([F:31])[F:30])[C:24]([N:34]=CN(C)C)=[C:23]([F:39])[CH:22]=3)[CH2:14][S:15](=[O:19])(=[O:18])[CH2:16]2)[O:11]C1=O)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[NH2:34][C:24]1[C:25]([CH2:27][C@H:28]([OH:33])[C:29]([F:32])([F:30])[F:31])=[CH:26][C:21]([CH2:20][C@H:13]2[C@H:12]([OH:11])[C@@H:17]([NH:9][CH2:8][C:7]3[CH:41]=[CH:42][CH:43]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[CH:6]=3)[CH2:16][S:15](=[O:19])(=[O:18])[CH2:14]2)=[CH:22][C:23]=1[F:39]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 131729363HCID 131729363, compound

Product 1

HCID 44625098HCID 44625098, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N′-[4-[(3aR*,7S*,7aS*)-3-(3-tert-butyl-benzyl)-2,5,5-trioxo-octahydro-1-oxa-5lambda*6*-thia-3-aza-inden-7-ylmethyl]-2-fluoro-6-((S)-3,3,3-trifluoro-2-hydroxy-propyl)-phenyl]-N,N-dimethyl-formamidine (0.1 g, 0.16 mmol) in anhydrous THF was added KOSi(CH3)4 (0.11 g, 0.8 mmol) and the reaction mixture was heated for 16 h at 60° C. The reaction mixture was added to cold 10% aq. K2CO3 solution and extracted with EtOAc. The combined organic layers were washed with 10% aq. K2CO3 solution and brine, dried over MgSO4, filtered and evaporated. The residue was converted into the hydrochloride salt with 1N HCl in Et2O and the precipitated salt was dried under reduced pressure to yield the title compound as a light yellow solid: TLC (CH2Cl2-MeOH-AcOH-H2O 180:20:2:1) Rf=0.46; HPLC RtA=1.79 min; ESIMS [M+H]+=547; HPLC RtA=1.22 min; ESIMS [M+H]+=337; 1H NMR (400 MHz, CDCl3+1% D2O): δ 7.34 (m, 3H), 7.12 (d, 1H), 6.79 (dd, 1H), 6.66 (s, 1H), 4.14 (m, 1H), 3.87 (dd, 1H), 3.74 (dd, 1H), 3.38 (dt, 1H), 2.8-3.2 (m, 6H), 2.72 (dd, 1H), 2.63 (t, 1H), 2.55 (dd, 1H), 2.29 (m, 1H), 1.34 (s, 9H).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with 10% aq. K2CO3 solution and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customthe precipitated salt was dried under reduced pressure

Sources & evidence

ORD record
ord-2a3a4f8a990d4954a8ffdfaaacd2166f
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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