Triethylamine → HCID 87947717, compound

HRID 1597306Notes

Reaction equation

HRID 1597306 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@@:9]2([CH3:33])[C:13](=[O:14])[N:12]([CH2:15][C:16]([NH:18][C@H:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:17])[C:11](=[O:32])[NH:10]2)=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:35][OH:36].C(N(CC)CC)C>C(O)C>[NH2:2][C:1](=[N:35][OH:36])[C:3]1[CH:8]=[CH:7][C:6]([C@@:9]2([CH3:33])[C:13](=[O:14])[N:12]([CH2:15][C:16]([NH:18][C@H:19]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:17])[C:11](=[O:32])[NH:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 15296941HCID 15296941, compound

Product 1

HCID 87947717HCID 87947717, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

b 120 l of ethanol were initially introduced into a vessel. At room temperature, 12 kg (26.786 mol) of ethyl (S)-3-(2-((S)-4-(4-cyanophenyl)-4-methyl-2,5-dioxoimidazolidin-1-yl)acetylamino)-3-phenylpropionate were added into the vessel, while stirring. 3.74 kg (53.813 mol) of hydroxylamine hydrochloride and 5.44 kg (7.45 l; 53.86 mol) of triethylamine were added. The reaction mixture was heated to reflux and stirred at 80° C. for 2 h. 90 l of ethanol were distilled off in vacuo at a bath temperature of 50° C. The remaining mixture was taken up in 220 l of ethyl acetate and this latter mixture was extracted three times with 50 l of water on each occasion. The ethyl acetate phase was evaporated down to 30 l in vacuo and at a bath temperature of 50° C. It was treated four times with 10 l of toluene on each occasion and evaporated to dryness.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. stirringstirred at 80° C. for 2 h
  4. distillation90 l of ethanol were distilled off in vacuo at a bath temperature of 50° C
  5. extractionthis latter mixture was extracted three times with 50 l of water on each occasion
  6. customThe ethyl acetate phase was evaporated down to 30 l in vacuo and at a bath temperature of 50° C
  7. additionIt was treated four times with 10 l of toluene on each occasion
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-09fe04a9f09744ac9d6cfe100d89c429
Source dataset
uspto-grants-2001_09
Patent number
US06294562B1

Reaction notes

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