HCID 86689288, compound → HCID 71620984, compound

HRID 537306Notes

Reaction equation

HRID 537306 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=O)[CH2:12][NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:6]([NH:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH:5]=1)[CH3:2]>CC(O)=O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]2[N:10]=[C:11]([CH2:12][NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:21]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:6]=2[CH:5]=1)[CH3:2]

Participants

3

Reactant 1

HCID 86689288HCID 86689288, compound

Product 1

HCID 71620984HCID 71620984, compoundYield 105.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 60 (3.0 g, 0.0088 mol) in AcOH (50 mL) was heated at 100° C. for 3 hr. The mixture was then concentrated in vacuo. To the residue was added EtOAc (100 mL) and 37% aqueous ammonia (15 mL). The organic phase was washed with saturated NaHCO3 (2×75 mL) and brine (75 mL), filtered through phase separation filter paper, and concentrated in vacuo to give 3.0 g of a red oil. The oil was chromatographed on 30 g of silica gel with 10 g of anhydrous sodium sulfate on top packed with hexanes. The column was eluted with 25 mL portions of 10% CH2Cl2 in hexanes for fractions 1-4, 10% EtOAc in hexanes for fractions 5-8, 15% EtOAc in hexanes for fractions 9-12, 20% EtOAc in hexanes for fractions 13-16, 25% EtOAc in hexanes for fractions 17-20, 30% EtOAc in hexanes for fractions 21-24 and 35% EtOAc in hexanes for fractions 25-28. The product was eluted in fractions 21-27 to give 0.7 g (25%) of compound #9 as a brown oil. HPLC analysis showed a purity of 96%. 1H NMR (300 MHz, CDCl3): δ 7.65 (d, 1H), 7.3 (m, 2H), 6.95-6.75 (m, 5H), 4.7 (brs, 1H), 4.5 (s, 2H), 4.1 (q, 2H), 3.95 (d, 2H), 2.3 (m, 1H), 1.5 (t, 3H), 1.0 (d, 6H) ppm.

Workup

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

Sources & evidence

ORD record
ord-c3ffd7e48f9e48a495cec6c511d2dbe1
Source dataset
uspto-grants-2014_10
Patent number
US08859780B2

Reaction notes

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