Triethylamine → HCID 58116569, compound

HRID 661243Notes

Reaction equation

HRID 661243 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[N:10]=[C:9]([CH:11]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:14][NH:13][CH2:12]2)[O:8][N:7]=1.C(N(CC)CC)C.Cl[C:36]([O:38][C:39]1[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=1)=[O:37]>ClCCl>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[N:10]=[C:9]([CH:11]2[CH2:16][CH:15]([C:17]3[CH:18]=[CH:19][C:20]([CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:21][CH:22]=3)[CH2:14][N:13]([C:36]([O:38][C:39]3[CH:40]=[CH:41][C:42]([N+:45]([O-:47])=[O:46])=[CH:43][CH:44]=3)=[O:37])[CH2:12]2)[O:8][N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 58116479HCID 58116479, compound

Product 1

HCID 58116569HCID 58116569, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 32 mg (0.08 mmol) of the compound from Example 66A in dichloromethane (1.0 ml) was admixed with 0.04 ml (29 mg, 0.29 mmol) of triethylamine and then, at 0° C., 17 mg (0.08 mmol) of 4-nitrophenyl chloroformate were added. The mixture was stirred at 0° C. for 2 h, then warmed to RT and stirred for 1 h. 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: 50.5 mg (79% of theory, purity 70%)

Workup

  1. temperaturewarmed to RT
  2. stirringstirred for 1 h
  3. washThe reaction solution was washed with saturated aqueous sodium hydrogencarbonate solution and water
  4. dry with materialthe organic phase was dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-868dbc10f21a42cebefdc0a655e81b5b
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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