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

HRID 565804Notes

Reaction equation

HRID 565804 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.[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

5

Reactant 3

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

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-PrMgCI solution in THF and, after 1 hr. at −20°, treated with a further 1.7 ml of the Grignard reagent. After a further 2½ 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. waitAfter a further 2½ 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-a47d2b7f0c3d4337bf159d46fdce66df
Source dataset
uspto-grants-2001_01
Patent number
US06172238B2

Reaction notes

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