Methyl chloroacetate → (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid methoxycarbonylmethyl ester

HRID 448627Notes

Reaction equation

HRID 448627 reaction equation
[CH3:1][O:2][C:3](=[O:6])[CH2:4]Cl.[C:7]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:12]=[CH:11][C:10]([CH2:13][C@@H:14]([NH:23]C(OC(C)(C)C)=O)[CH2:15][C@:16]([CH2:21][OH:22])([CH3:20])[C:17]([OH:19])=[O:18])=[CH:9][CH:8]=1.CCN(CC)CC>CC(C)=O>[CH3:1][O:2][C:3]([CH2:4][O:19][C:17](=[O:18])[C@@:16]([CH2:21][OH:22])([CH3:20])[CH2:15][C@H:14]([NH2:23])[CH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:8][CH:9]=1)=[O:6]

Participants

5

Reactant 3

HCID 7295Methyl chloroacetateHCID 8471TriethylamineHCID 68181022(2S,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-2-methyl-pentanoic acid

Product 1

HCID 68181051(2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid methoxycarbonylmethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Chloroacetic acid methyl ester (34 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 methoxycarbonylmethyl 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-9c25ddfe325d48a1a7e977e9b0cf2863
Source dataset
uspto-grants-2013_07
Patent number
US08481044B2

Reaction notes

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