Triethylamine → HCID 58116539, compound

HRID 661239Notes

Reaction equation

HRID 661239 reaction equation
[CH2:1]([O:3][C:4]1[N:8]=[C:7]([CH:9]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[CH2:12][NH:11][CH2:10]2)[O:6][N:5]=1)[CH3:2].C(N(CC)CC)C.Cl[C:34]([O:36][C:37]1[CH:42]=[CH:41][C:40]([N+:43]([O-:45])=[O:44])=[CH:39][CH:38]=1)=[O:35]>ClCCl>[CH2:1]([O:3][C:4]1[N:8]=[C:7]([CH:9]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=3)[CH2:12][N:11]([C:34]([O:36][C:37]3[CH:38]=[CH:39][C:40]([N+:43]([O-:45])=[O:44])=[CH:41][CH:42]=3)=[O:35])[CH2:10]2)[O:6][N:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 58116570HCID 58116570, compound

Product 1

HCID 58116539HCID 58116539, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 52 mg (0.14 mmol) of the compound from Example 61A in dichloromethane (1.6 ml) was admixed with 0.07 ml (49.7 mg, 0.49 mmol) of triethylamine and then, at 0° C., 28 mg (0.14 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: 75.8 mg (95% of theory)

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-30b037a245e448eea377f2365316fb1f
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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