Lithium Hydroxide → HCID 21878903, compound

HRID 724587Notes

Reaction equation

HRID 724587 reaction equation
C[O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][N:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:13](=[O:20])[CH:12]=2)=[CH:7][CH:6]=1.[Li+].[OH-]>C1COCC1.CO.[OH-].[Na+]>[C:16]([N:14]1[C:13](=[O:20])[CH:12]=[C:11]([C:8]2[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:21])=[O:2])=[CH:10][CH:9]=2)[S:15]1)([CH3:19])([CH3:17])[CH3:18]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 58746473HCID 58746473, compound

Product 1

HCID 21878903HCID 21878903, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1-C (0.35 g, 1.2 mmol) and 10% LiOH (0.8 mL, 3.5 mmol) in THF (4 mL) and methanol (1 mL) was stirred at 25° C. for 2 h. The reaction mixture was diluted with 1 N NaOH (75 mL) and extracted with CH2Cl2 (3×25 mL). The aqueous layer was adjusted to pH˜2 with 10% HCl and extracted with EtOAc (3×50 mL). The combined organic layers were dried with Na2SO4, filtered, and concentrated in vacuo to yield 1-D as a brown solid (quantitative) which was used in the next step without further purification. 1H NMR (400 MHz, CD3OD): δ 7.57 (d, J=8.2 Hz, 2H), 7.42 (d, J=8.0 Hz, 2H), 6.51 (s, 1H), 3.67 (s, 2H), 1.68 (s, 9H); LCMS found for C15H16NO3S (M−H)−: m/z=290.

Workup

  1. extractionextracted with CH2Cl2 (3×25 mL)
  2. extractionextracted with EtOAc (3×50 mL)
  3. dry with materialThe combined organic layers were dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto yield 1-D as a brown solid (quantitative) which
  7. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-7b3788d6b4e444108635fb8109692284
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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