Triethylamine → HCID 58116467, compound

HRID 2091774Notes

Reaction equation

HRID 2091774 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 50A in dichloromethane (44 ml) was admixed with 1.84 ml (1.34 g, 13.2 mmol) of triethylamine and then admixed at 0° C. 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. washThe reaction solution was washed with saturated aqueous sodium hydrogencarbonate solution and water
  2. dry with materialthe organic phase was dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. additionYield: 1.93 g (92% of theory, purity 81%, 2:1 mixture of methyl and ethyl ester)

Sources & evidence

ORD record
ord-ac270a61218c4725841ce3b78e3524d6
Source dataset
uspto-grants-2013_05
Patent number
US08440657B2

Reaction notes

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