Ammonium Chloride → HCID 118098675, compound

HRID 708803Notes

Reaction equation

HRID 708803 reaction equation
[CH:1]1([S:4][C:5]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][C:6]=2[CH2:7][N:8]([CH3:16])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3][CH2:2]1.[Cl-].[NH4+]>C(O)C.[Zn]>[NH2:21][C:18]1[CH:19]=[CH:20][C:5]([S:4][CH:1]2[CH2:3][CH2:2]2)=[C:6]([CH:17]=1)[CH2:7][N:8]([CH3:16])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 59315091HCID 59315091, compound

Product 1

HCID 118098675HCID 118098675, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

Zinc (1.063 g, 16.25 mmol) was added to a mixture of Intermediate 6B (1 g, 2.95 mmol) and ammonium chloride (3.16 g, 59.1 mmol) in ethanol (10 mL). The mixture was stirred for 3 h at rt and concentrated. Na2CO3 (sat'd, 50 mL) and EtOAc (50 mL) was added and stirred for 1 h. The phases were separated and the aqueous layer was extracted with EtOAc (2×50 mL). The organics were combined, washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (loading in chloroform, 0% to 50% ethyl acetate in hexane over 30 min using a 40 g silica gel cartridge) to yield Intermediate 6C (600 mg, 1.945 mmol, 65.8% yield) as a yellow oil. 1H NMR (400 MHz, chloroform-d) δ ppm 7.35 (1H, d, J=8.35 Hz), 6.58 (1H, dd, J=8.13, 2.42 Hz), 6.52 (1H, d, J=30.32 Hz), 4.45-4.61 (2H, m), 3.68 (2H, br. s.), 2.75-2.91 (3H, m), 2.03-2.15 (1H, m), 1.41-1.55 (9H, m), 0.83-0.97 (2H, m), 0.64 (2H, q, J=4.54 Hz).

Workup

  1. concentrationconcentrated
  2. additionNa2CO3 (sat'd, 50 mL) and EtOAc (50 mL) was added
  3. stirringstirred for 1 h
  4. customThe phases were separated
  5. extractionthe aqueous layer was extracted with EtOAc (2×50 mL)
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe crude product was purified by flash chromatography (loading in chloroform
  10. wait0% to 50% ethyl acetate in hexane over 30 min using

Sources & evidence

ORD record
ord-139141ec448c4b4e9a668f9d15957710
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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