Sodium Bicarbonate → (2S*,3R*)-3-hydroxy-4,4-dimethyl-2-[(4-phenyl-phenyl)-methoxy-carbonylamino]-pentanoic acid

HRID 530579Notes

Reaction equation

HRID 530579 reaction equation
[NH2:1][C@@H:2]([C@H:6]([OH:11])[C:7]([CH3:10])([CH3:9])[CH3:8])[C:3]([OH:5])=[O:4].C([O-])(O)=O.[Na+].[C:17](=O)([O-:38])[O:18][C:19]1C(C)=C(C2C=CC(C3C=CC=CC=3)=CC=2)C=CN=1.[C:40]1([C:46]2[CH:51]=[CH:50][C:49](C3C=CN(C([O-])=O)C(=O)C=3C)=[CH:48][CH:47]=2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>O.C1COCC1>[OH:11][C@H:6]([C:7]([CH3:8])([CH3:10])[CH3:9])[C@H:2]([N:1]([C:49]1[CH:48]=[CH:47][C:46]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[CH:51][CH:50]=1)[C:17]([O:18][CH3:19])=[O:38])[C:3]([OH:5])=[O:4]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 2725116(2S,3R)-2-Amino-3-Hydroxy-4,4-Dimethylpentanoic AcidHCID 86699987(4-Phenylphenyl)-methyl-2-pyridyl carbonateHCID 86699989(4-Phenylphenyl)-methyl-2-oxopyridine-1-carboxylate

Product 1

HCID 86700029(2S*,3R*)-3-hydroxy-4,4-dimethyl-2-[(4-phenyl-phenyl)-methoxy-carbonylamino]-pentanoic acidYield 21%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of (2S*,3R*)-2-amino-3-hydroxy-4,4-dimethyl-pentanoic acid (0.353 g, 2.19 mmol) and NaHCO3 (0.184 g, 0.84 mmol) in H2O (15 mL), at rt, the isomeric mixture containing (4-phenylphenyl)-methyl-2-pyridyl carbonate and (4-phenylphenyl)-methyl-2-oxopyridine-1-carboxylate (0.815 g, 2.2 mmol) [prepared as for example 17, step 1] in THF (15 mL) was added. After 15 h at rt, the crude mixture was rotary evaporated to remove the organics and subsequently extracted with Et2O (3×20 mL). The aqueous phase was acidified with 2.0 M HCl solution to pH 2-3 and subsequently extracted with AcOEt (3×20 mL). The organic fraction was dried over Na2SO4, filtered and concentrated to dryness to afford the title compound (0.181 g, 21%), which was used in the next step without further purification. MS (ESI) m/z: 410 [M−K]+; (ESI) m/z: 370 [M−H]−.

Workup

  1. additionwas added
  2. customthe crude mixture was rotary evaporated
  3. customto remove the organics and
  4. extractionsubsequently extracted with Et2O (3×20 mL)
  5. extractionsubsequently extracted with AcOEt (3×20 mL)
  6. dry with materialThe organic fraction was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2ba4e580051244d9bc1a0833efe5922e
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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