Ammonium Chloride → 1-[2(R)-[1(R)-(benzyloxycarbamoyl)-2-(3,4,4-trimethyl-2,5-dioxo-1-imidazolidinyl)ethyl]-3-cyclopentylpropionyl)piperidine

HRID 378587Notes

Reaction equation

HRID 378587 reaction equation
CO[C:3]([C@H:5]([C@@H:17]([CH2:26][CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)[C:18]([N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:19])[CH2:6][N:7]1[C:11](=[O:12])[C:10]([CH3:14])([CH3:13])[N:9]([CH3:15])[C:8]1=[O:16])=[O:4].Cl.[CH2:33]([O:40][NH2:41])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C([Mg]Cl)(C)C.[Cl-].[NH4+]>C1COCC1>[CH2:33]([O:40][NH:41][C:3]([C@H:5]([C@@H:17]([CH2:26][CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31]1)[C:18]([N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:19])[CH2:6][N:7]1[C:11](=[O:12])[C:10]([CH3:14])([CH3:13])[N:9]([CH3:15])[C:8]1=[O:16])=[O:4])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 102312Benzyloxyamine hydrochlorideHCID 183920571-[2(R)-[1(R)-(methoxycarbonyl)-2-(3,4,4-trimethyl-2,5-dioxo-1-imidazolidinyl)ethyl]-3-cyclopentylpropionyl]piperdineHCID 178418918HCID 178418918, compound

Product 1

HCID 543913361-[2(R)-[1(R)-(benzyloxycarbamoyl)-2-(3,4,4-trimethyl-2,5-dioxo-1-imidazolidinyl)ethyl]-3-cyclopentylpropionyl)piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.10 g of methyl ester from Example 10 and 568 mg of O-benzylhydroxylamine hydrochloride in 7 ml of THF was treated at -20° with 3.5 ml of a 2M i-PrMgCl solution in THF and, after 1 hr. at -20°, treated with a further 1.7 ml of the Grignard reagent. After a further 21/2 hrs. at -20° the mixture was treated with ammonium chloride solution and extracted with methylene chloride. The extracts were dried and concentrated. The residue was crystallized from t-butyl methyl ether/hexane and the crystallizate was dried, there being obtained 1-[2(R)-[1(R)-(benzyloxycarbamoyl)-2-(3,4,4-trimethyl-2,5-dioxo-1-imidazolidinyl)ethyl]-3-cyclopentylpropionyl)piperidine VII, m.p. 135-137°.

Workup

  1. custom2 hrs
  2. extractionextracted with methylene chloride
  3. customThe extracts were dried
  4. concentrationconcentrated
  5. customThe residue was crystallized from t-butyl methyl ether/hexane
  6. customthe crystallizate was dried

Sources & evidence

ORD record
ord-1e710380379e46929a78074ff983f590
Source dataset
uspto-grants-2000_02
Patent number
US06031103

Reaction notes

Loading…