Acetyl chloride → HCID 70160951, compound

HRID 842615Notes

Reaction equation

HRID 842615 reaction equation
Br.[CH3:2][O:3][C:4]1[C:5]([N+:24]([O-:26])=[O:25])=[C:6]([CH:21]=[CH:22][CH:23]=1)[O:7][CH2:8][CH:9]([OH:20])[CH2:10][NH:11][C@@H:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13].[C:27](Cl)(=[O:29])[CH3:28].C(N(CC)CC)C>ClCCl>[CH3:2][O:3][C:4]1[C:5]([N+:24]([O-:26])=[O:25])=[C:6]([CH:21]=[CH:22][CH:23]=1)[O:7][CH2:8][C:9](=[O:20])[CH2:10][N:11]([C@@H:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13])[C:27](=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 70160683HCID 70160683, compound

Product 1

HCID 70160951HCID 70160951, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

The product from Example 7B (33.0 g, 77.6 mmol) in dichloromethane (600 mL) at 0 ° C. was treated sequentially with acetyl chloride (6.4 g, 81.0 mmol) and triethylamine (23.6 g,233 mmol) in dichloromethane (50 mL), stirred for 1 hour at 0° C., and quenched with 1M NaOH. The organic layer was washed with brine, dried (MgSO4), and concentrated to provide the title compound. 1H NMR (300 MHz, CDCl3) δ1.60 (d, 3H), 2.29 (s, 3H), 3.70 (d, 1H),3.86 (s, 3H), 4.14 (d, 1H), 4.55 (d, 1H), 4.73 (d, 1H), 5.15 (q, 1H), 6.55 (d, 1H), 6.65 (d, 1H), 7.20-7.42 (m, 6H).

Workup

  1. customquenched with 1M NaOH
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c997057a744946b786faa4b3b594cda2
Source dataset
uspto-grants-2002_04
Patent number
US06376488B1

Reaction notes

Loading…