Triethylamine → HCID 178513886, compound

HRID 2294729Notes

Reaction equation

HRID 2294729 reaction equation
C(S(C[C@@H](CC1C=CC=CC=1)C(N[C@@H:13]([CH2:32][C:33]1[N:34]=[CH:35][NH:36][CH:37]=1)[C:14]([NH:16][C@@H](CC1CCCCC1)[C@@H](O)C(C1CC1)=O)=[O:15])=O)(=O)=O)(C)(C)C.Cl.NO.C(N(CC)CC)C>CO>[NH:36]1[CH:37]=[C:33]([CH2:32][CH2:13][C:14]([NH2:16])=[O:15])[N:34]=[CH:35]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 178455617HCID 178455617, compound

Product 1

HCID 178513886HCID 178513886, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 62.8 mg (0.1 mmol) of (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R)-1-(cyclohexylmethyl)-3-cyclopropyl-2-hydroxy-3-oxopropyl]imidazole-4-propionamide, 12 mg (0.2 mmol) of hydroxylamine hydrochloride and 0.027 ml (0.2 mmol) of triethylamine in 2.5 ml of methanol is heated to reflux for 20 hours. After the usual working-up the crude product obtained is purified by chromatography on 10 g of silica gel using a 8:1 mixture of methylene chloride and methanol as the eluting agent. There are obtained 28 mg of (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,E/Z=2:1)-1-(cyclohexylmethyl)-3-cyclopropyl-2-hydroxy-3-(hydroxyimino)propyl]imidazole-4-propionamide as an amorphous solid; MS: 644 (M+H)+.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 20 hours
  3. customobtained
  4. customis purified by chromatography on 10 g of silica gel using
  5. additiona 8:1 mixture of methylene chloride and methanol as the eluting agent

Sources & evidence

ORD record
ord-bcaec6678cbe49b7bf7c77685fec27dd
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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