HCID 86689286, compound → HCID 71621465, compound

HRID 537304Notes

Reaction equation

HRID 537304 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][CH2:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][C:12]=2[NH:20][CH2:21][CH:22]([CH3:24])[CH3:23])=O)=[CH:4][CH:3]=1>CC(O)=O>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][CH2:7][C:8]2[N:20]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:12]3[CH:13]=[C:14]([O:17][CH2:18][CH3:19])[CH:15]=[CH:16][C:11]=3[N:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86689286HCID 86689286, compound

Product 1

HCID 71621465HCID 71621465, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 58a (3.5 g, 0.0093 mol) in AcOH (50 mL) was heated at 100° C. for 1 hr. The reaction mixture was concentrated in vacuo, and to the residue was added CH2Cl2 (100 mL) and 37% aqueous ammonia (15 mL). The organic phase was washed with saturated NaHCO3 (2×75 mL) and brine (1×75 mL), filtered through phase separation filter paper, and concentrated in vacuo to give 3.0 g of a pink solid. The solid was chromatographed on 50 g of silica gel with 10 g anhydrous sodium sulfate on top packed with hexanes. The column was eluted with 25 mL portions of hexanes for fractions 1-4, 25% EtOAc in hexanes for fractions 5-8, and 35% EtOAc in hexanes for fractions 9-20. The product eluted in fractions 11-20 to give 2.5 g (70%) of Compound #7 as a tan solid. HPLC analysis showed a purity of 97%. 1H NMR (300 MHz, CDCl3): δ 7.7 (d, 1H), 7.3-6.8 (m, 6H), 5.35 (s, 2H), 4.1 (m, 4H), 2.3 (m, 1H), 1.45 (t, 3H), 1.0 (d, 6H) ppm.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionto the residue was added CH2Cl2 (100 mL) and 37% aqueous ammonia (15 mL)
  3. washThe organic phase was washed with saturated NaHCO3 (2×75 mL) and brine (1×75 mL)
  4. filtrationfiltered through phase separation
  5. filtrationfilter paper
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-088c93230f234f4a9fe7928148f3e49c
Source dataset
uspto-grants-2014_10
Patent number
US08859780B2

Reaction notes

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