Triethylamine → (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid dimethylcarbamoylmethyl ester

HRID 535184Notes

Reaction equation

HRID 535184 reaction equation
Cl[CH2:2][C:3]([N:5]([CH3:7])[CH3:6])=[O:4].[C:8]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:13]=[CH:12][C:11]([CH2:14][C@@H:15]([NH:24]C(OC(C)(C)C)=O)[CH2:16][C@:17]([CH2:22][OH:23])([CH3:21])[C:18]([OH:20])=[O:19])=[CH:10][CH:9]=1.CCN(CC)CC>CC(C)=O>[CH3:6][N:5]([CH3:7])[C:3]([CH2:2][O:20][C:18](=[O:19])[C@@:17]([CH2:22][OH:23])([CH3:21])[CH2:16][C@H:15]([NH2:24])[CH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:9][CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 758862-chloro-N,N-dimethylacetamideHCID 68181022(2S,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-2-methyl-pentanoic acid

Product 1

HCID 68181070(2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid dimethylcarbamoylmethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Chloro-N,N-dimethylacetamide (40 μL, 387 μmol) was added to a mixture of (2S,4R)-5-biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-2-methyl-pentanoic acid (100 mg, 242 μmol) and Et3N (35 μL, 254 μmol) in acetone (10 mL). The mixture was refluxed for 24 hours and the reaction monitored for completion. When the reaction was complete, the product was purified ((Interchim reverse phase chromatography column) the solvent was removed under vacuum to yield (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid dimethylcarbamoylmethyl ester.

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. customthe product was purified ((Interchim reverse phase chromatography column) the solvent
  3. customwas removed under vacuum

Sources & evidence

ORD record
ord-74732be78f1547d88b58e8ad18d59e09
Source dataset
uspto-grants-2014_10
Patent number
US08853427B2

Reaction notes

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