Ethanol → HCID 178473919, compound

HRID 1157358Notes

Reaction equation

HRID 1157358 reaction equation
[CH:1]1[CH:6]=[C:5]([C:7]([C:17]2[CH:22]=[C:21]([I:23])[C:20]([O-:24])=[C:19]([I:25])[CH:18]=2)=[C:8]2[CH:14]=[C:13]([I:15])[C:11](=[O:12])[C:10]([I:16])=[CH:9]2)[C:4]([C:26]([O-:28])=[O:27])=[CH:3][CH:2]=1.[Na+:29].[Na+].C(OC([N:36]1[CH2:41][CH2:40][N:39]([C:42](=[O:54])[C@H:43]([CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[C:48]([C:52]#[N:53])[CH:47]=2)[NH2:44])[CH2:38][CH2:37]1)=O)C.Cl.[NH2:56][OH:57].C(N(CC)CC)C.[CH2:65]([OH:67])[CH3:66]>>[CH:1]1[CH:6]=[C:5]([C:7]([C:8]2[CH:9]=[C:10]([I:16])[C:11]([O-:12])=[C:13]([I:15])[CH:14]=2)=[C:17]2[CH:18]=[C:19]([I:25])[C:20](=[O:24])[C:21]([I:23])=[CH:22]2)[C:4]([C:26]([O-:28])=[O:27])=[CH:3][CH:2]=1.[Na+:29].[Na+:29].[CH2:65]([O:67][N:36]1[CH2:37][CH2:38][N:39]([C:42](=[O:54])[C@H:43]([CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[C:48]([C:52](=[NH:53])[NH:56][OH:57])[CH:47]=2)[NH2:44])[C:40](=[C:26]=[O:28])[CH2:41]1)[CH3:66]

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 131727689HCID 131727689, compound

Product 1

HCID 178473919HCID 178473919, compound

Procedure

TIPPS-3-cyano-(L)-phenylalanine-4-ethoxycarbonylpiperazide (130 g; 196 mmol; 90% purity), hydroxylamine hydrochloride (22 g; 313 mmol) and triethylamine (63 g; 626 mmol) were dissolved in 470 ml of ethanol and stirred at RT for 1 day. After evaporating the solvent, the residue was taken up in 300 ml of ethyl acetate and extracted in each case 2× with 5% KHSO4, 5% NaHCO3 and distilled water. After evaporating the solvent, the crude product was dried under vacuum and then recrystallized from ethyl acetate/ether.

Workup

  1. customAfter evaporating the solvent
  2. extractionextracted in each case 2× with 5% KHSO4, 5% NaHCO3
  3. distillationdistilled water
  4. customAfter evaporating the solvent
  5. dry with materialthe crude product was dried under vacuum
  6. customrecrystallized from ethyl acetate/ether

Sources & evidence

ORD record
ord-394843a52e404cee921885b8d7036537
Source dataset
uspto-grants-2010_10
Patent number
US07807681B2

Reaction notes

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