Dichloromethane → HCID 178422279, compound

HRID 1914839Notes

Reaction equation

HRID 1914839 reaction equation
CO[C:3]([C:5]1[CH:6]=[N:7][C:8]2[N:9]([N:21]=[C:22]([CH3:24])[CH:23]=2)[C:10]=1[NH:11][C:12](=[O:20])[CH2:13]C1C=CC=CC=1)=[O:4].C1COCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C(Cl)Cl>O>[CH3:24][C:22]1[CH:23]=[C:8]2[N:7]=[CH:6][C:5]3[C:3]([OH:4])=[CH:13][C:12]([OH:20])=[N:11][C:10]=3[N:9]2[N:21]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 2724254Sodium bis(trimethylsilyl)amideHCID 58034449HCID 58034449, compound

Product 1

HCID 178422279HCID 178422279, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 250 mL round bottom flask containing Compound (20-1) (1.62 g, 5.0 mmol, 1 eq.), THF (30 mL), and NaHMDS (7.5 mL, 7.5 mmol, 1.5 eq.) was stirred at room temperature for 2 h. The reaction was treated with CH2Cl2 (30 mL) and water (40 mL). The aqueous phase was extracted with CH2Cl2 (2×15 mL). The water layer was acidified with concentrated HCl (˜10 mL). The precipitated solid was filtered and washed with CH2Cl2 (4 mL) to furnish Compound (20-2) as a yellowish solid. The acidified water layer was extracted with 5% MeOH in CH2Cl2 (3×25 mL). The combined organic phases were dried over Na2SO4. After filtration and concentration, the residue was purified by silica gel chromatography using MeOH and CH2Cl2 as the mobile phases to furnish Compound (20-2) as a yellowish solid.

Workup

  1. extractionThe aqueous phase was extracted with CH2Cl2 (2×15 mL)
  2. filtrationThe precipitated solid was filtered
  3. washwashed with CH2Cl2 (4 mL)

Sources & evidence

ORD record
ord-a02c4f136335466e9c991810291bc343
Source dataset
uspto-grants-2013_12
Patent number
US08614221B2

Reaction notes

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