Triethylamine → HCID 58116467, compound

HRID 661245Notes

Reaction equation

HRID 661245 reaction equation
[F:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][NH:15][CH2:14][CH:13]([C:17]([O:19][CH3:20])=[O:18])[CH2:12]2)=[CH:7][CH:6]=1)([F:4])[CH3:3].C(N(CC)CC)C.Cl[C:29]([O:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1)=[O:30]>ClCCl>[F:1][C:2]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[CH2:16][N:15]([C:29]([O:31][C:32]3[CH:33]=[CH:34][C:35]([N+:38]([O-:40])=[O:39])=[CH:36][CH:37]=3)=[O:30])[CH2:14][CH:13]([C:17]([O:19][CH3:20])=[O:18])[CH2:12]2)=[CH:9][CH:10]=1)([F:4])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 58116554HCID 58116554, compound

Product 1

HCID 58116467HCID 58116467, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.30 g (3.78 mmol, purity 82%) of the compound from Example 70A in dichloromethane (44 ml) was admixed with 1.84 ml (1.34 g, 13.2 mmol) of triethylamine and then, at 0° C., admixed with 762 mg (3.78 mmol) of 4-nitrophenyl chloroformate. The mixture was warmed to RT and stirred for 2 days. The reaction solution was washed with saturated aqueous sodium hydrogencarbonate solution and water, and the organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. Yield: 1.93 g (92% of theory, purity 81%, 2:1 mixture of methyl and ethyl ester)

Workup

  1. customat 0° C.
  2. washThe reaction solution was washed with saturated aqueous sodium hydrogencarbonate solution and water
  3. dry with materialthe organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionYield: 1.93 g (92% of theory, purity 81%, 2:1 mixture of methyl and ethyl ester)

Sources & evidence

ORD record
ord-90a2e846b8be4cb2a36eb6c35d225626
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

Loading…