Hydrochloric Acid → HCID 86603750, compound

HRID 226445Notes

Reaction equation

HRID 226445 reaction equation
[C:1]([O:5][C:6]([N:8]([C@@H:22]1[CH2:26][CH2:25][N:24]([CH:27]2[CH2:32][C:31]([CH3:34])([CH3:33])[NH:30][C:29]([CH3:36])([CH3:35])[CH2:28]2)[CH2:23]1)[C:9]1[N:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19]CC)=O)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:38][OH:39].C[O-].[K+].Cl>CO>[OH:39][NH:38][C:17](=[O:19])/[CH:16]=[CH:15]/[C:12]1[CH:11]=[CH:10][C:9]([N:8]([C@@H:22]2[CH2:26][CH2:25][N:24]([CH:27]3[CH2:28][C:29]([CH3:36])([CH3:35])[NH:30][C:31]([CH3:34])([CH3:33])[CH2:32]3)[CH2:23]2)[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[N:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 23664618Potassium methoxideHCID 86603751HCID 86603751, compound

Product 1

HCID 86603750HCID 86603750, compoundYield 39.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of ethyl (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-1-(2,2,6,6-tetramethyl-4-piperidinyl)-3-pyrrolidinyl]amino}-3-pyridinyl)acrylate (265 mg, 0.529 mmol) in methanol (5 mL) was added hydroxylamine hydrochloride (184 mg, 2.65 mmol) at ambient temperature. To this mixture was added 1N potassium methoxide in methanol (5.29 mL, 5.29 mmol) dropwise in an ice bath and the resulting mixture was stirred at ambient temperature for three hours. To the mixture was added 1N hydrogen chloride to neutralize the solution. The solvent was removed in vacuo and the residue was desalted using ion-exchange resin. The crude product was purified by preparative high-pressure liquid chromatography to afford tert-butyl {5-[(1E)-3-(hydroxyamino)-3-oxo-1-propen-1-yl]-2-pyridinyl}[(3R)-1-(2,2,6,6-tetramethyl-4-piperidinyl)-3-pyrrolidinyl]carbamate (103 mg) as a colorless wax.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe crude product was purified by preparative high-pressure liquid chromatography

Sources & evidence

ORD record
ord-57813a23757f4cdd949b3469019914e4
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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