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

HRID 523407Notes

Reaction equation

HRID 523407 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].[C:11]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:16]=[CH:15][C:14]([CH2:17][C@@H:18]([NH:27]C(OC(C)(C)C)=O)[CH2:19][C@:20]([CH2:25][OH:26])([CH3:24])[C:21]([OH:23])=[O:22])=[CH:13][CH:12]=1.CCN(CC)CC>CC(C)=O>[N:5]1([C:3](=[O:4])[CH2:2][O:23][C:21](=[O:22])[C@@:20]([CH2:25][OH:26])([CH3:24])[CH2:19][C@H:18]([NH2:27])[CH2:17][C:14]2[CH:15]=[CH:16][C:11]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:12][CH:13]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74040Morpholine, 4-(chloroacetyl)-HCID 68181022(2S,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-2-methyl-pentanoic acid

Product 1

HCID 68181046(2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid 2-morpholin-4-yl-2-oxo-ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-(2-chloroacetyl)morpholine (63 mg, 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 2-morpholin-4-yl-2-oxo-ethyl 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-791ebb930e684d2ba0ddc3533779a20a
Source dataset
uspto-grants-2016_05
Patent number
US09334245B2

Reaction notes

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