Sodium Bicarbonate → HCID 87464024, compound

HRID 1260366Notes

Reaction equation

HRID 1260366 reaction equation
O[C@@H:2]1[CH2:6][CH2:5][N:4]([C:7](/[N:9]=[C:10]2\[S:11][C:12]([CH3:29])=[CH:13][N:14]\2[C:15]2[CH:28]=[CH:27][C:18]3[O:19][C:20]([F:26])([F:25])[C:21]([F:24])([F:23])OC=3[CH:16]=2)=[O:8])[CH2:3]1.COCCN(S(F)(F)[F:40])CCOC.[C:43](=[O:46])(O)[O-].[Na+]>C(Cl)Cl>[F:40][C@H:2]1[CH2:6][CH2:5][N:4]([C:7](/[N:9]=[C:10]2\[S:11][C:12]([CH3:29])=[CH:13][N:14]\2[C:15]2[CH:28]=[CH:27][C:18]3[O:19][C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[O:46][C:43]=3[CH:16]=2)=[O:8])[CH2:3]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 87464405HCID 87464405, compound

Product 1

HCID 87464024HCID 87464024, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3R)-3-hydroxy-N-[(2Z)-5-methyl-3-(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)-1,3-thiazol-2(3H)-ylidene]pyrrolidine-1-carboxamide (Example 109, 0.1 g, 0.23 mmol) in dry CH2Cl2 (5 mL) was treated with bis(2-methoxyethyl)aminosulfur trifluoride (0.056 g, 0.25 mmol) After 2 hours at room temperature, the mixture was neutralized by dropwise addition of a saturated solution of sodium bicarbonate. The mixture was washed with water and brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified over silica using CH2Cl2 as eluant. 1H NMR (CDCl3) δ ppm 2.00 (2 H), 2.25 (3 H), 3.35-3.85 (4 H), 5.15-5.30 (1 H), 6.60 (1 H), 7.20 (1 H), 7.35 (1 H), 7.45 (1 H); MS (ESI) m/z 436(M+H)+.

Workup

  1. washThe mixture was washed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified over silica

Sources & evidence

ORD record
ord-f45c1043296441c2bed5fcc7a3b83b5f
Source dataset
uspto-grants-2013_06
Patent number
US08470813B2

Reaction notes

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