Water → (2R,3S)-3-hydroxy-2-[methyl-(5-phenylpentoxycarbonyl)-amino]-butanoic acid

HRID 530531Notes

Reaction equation

HRID 530531 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[C:12]([C@H:15]([NH2+:19][CH3:20])[C@@H:16](O)[CH3:17])([OH:14])=[O:13].[C:21]([O-:24])(O)=[O:22].[Na+].[C:26]1([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]C2C(=O)N(C([O-])=O)C=CC=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[OH2:47]>C1COCC1>[OH:47][C@@H:16]([CH3:17])[C@@H:15]([N:19]([CH3:20])[C:21]([O:24][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:22])[C:12]([OH:14])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 866999375-Phenyl-pentyl-2-oxopyridine-1-carboxylateHCID 86699955[(1R,2S)-1-carboxy-2-hydroxy-propyl]-methyl-ammonium toluene-4-sulfonate

Product 1

HCID 73294311(2R,3S)-3-hydroxy-2-[methyl-(5-phenylpentoxycarbonyl)-amino]-butanoic acidYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of [(1R,2S)-1-carboxy-2-hydroxy-propyl]-methyl-ammonium toluene-4-sulfonate (0.1 g, 0.33 mmol) and NaHCO3 (0.05 g, 0.65 mmol) in H2O (1.0 mL), the isomeric mixture containing 5-phenyl-pentyl-2-pyridyl-carbonate and 5-phenyl-pentyl-2-oxopyridine 1-carboxylate (0.14 g, 0.49 mmol) [prepared as for Example 37, step 1] in THF (1.0 mL) was added. After 15 h at rt, the crude mixture was rotary evaporated to remove the organics, diluted and subsequently extracted with Et2O (3×5 mL). The aqueous phase was acidified with 2.0 M HCl solution to pH 2-3 and subsequently extracted with EtOAc (3×10 mL). The organic fraction was dried over Na2SO4, filtered and concentrated to dryness to afford the title compound (0.05 g, 45%), as a mixture of two rotamers (1.5:1 ratio), as a colorless sticky oil. 1H NMR (DMSO-d6) δ 1.07 (d, J=6.3 Hz, 6H), 1.27-1.40 (m, 4H), 1.51-1.66 (m, 8H), 2.53-2.60 (m, 4H), 2.90 (s, 3H, minor rotamer), 2.91 (s, 3H, major rotamer), 3.92-4.02 (m, 4H), 4.16-4.27 (m, 2H), 4.32 (d, J=5.8 Hz, 1H, minor rotamer), 4.47 (d, J=5.4 Hz, 1H, major rotamer), 7.13-7.31 (m, 10H).

Workup

  1. additionwas added
  2. customthe crude mixture was rotary evaporated
  3. customto remove the organics,
  4. additiondiluted
  5. extractionsubsequently extracted with Et2O (3×5 mL)
  6. extractionsubsequently extracted with EtOAc (3×10 mL)
  7. dry with materialThe organic fraction was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ba74d9b47ab441d4bfbf5df4ce51cc10
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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