Hydrochloric Acid → HCID 178472571, compound

HRID 2279595Notes

Reaction equation

HRID 2279595 reaction equation
C([Si](CC)(CC)[O:4][C@H:5]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:6][CH2:7][CH:8]([C:13]([O:15]C)=O)[C:9]([O:11]C)=O)C.[O:26]1[CH2:31][CH2:30][CH:29]([NH:32][C:33]([NH2:35])=[NH:34])[CH2:28][CH2:27]1.CC[O-].[Na+].Cl.O1CCOCC1>CCO>[CH2:20]([O:19][C:17](=[O:18])[C@@H:5]([OH:4])[CH2:6][CH2:7][C:8]1[C:9]([OH:11])=[N:34][C:33]([NH:32][CH:29]2[CH2:30][CH2:31][O:26][CH2:27][CH2:28]2)=[N:35][C:13]=1[OH:15])[CH3:21]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 2723922Sodium ethoxideHCID 86705577HCID 86705577, compoundHCID 178512590HCID 178512590, compound

Product 1

HCID 178472571HCID 178472571, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 398 (3.75 g, 9.46 mmol), 24 (1.63 g, 11.4 mmol), EtOH (30 mL) and NaOEt (3.86 g, 11.4 mmol) was heated to 85° C. and stirred overnight. The reaction was cooled to RT and quenched reaction by addition of 4N HCl in dioxane (2.37 mL, 9.46 mmol) and the solution concentrated. The crude product was purified by reverse phase chromatography (Biotage 40 M C18 using a C18 samplet loaded using water) eluting with a MeCH/H2O chromatography (0-60% MeCN) over 30 column volumes to afford 1.25 g (37%) of (S)-ethyl-4-(4,6-dihydroxy-2-(tetrahydro-2H-pyran-4-ylamino) pyrimidin-5-yl)-2-hydroxybutanoate (400): MS m/z (APCI-pos) M+1=342.1.

Workup

  1. customquenched
  2. customreaction
  3. concentrationthe solution concentrated
  4. customThe crude product was purified by reverse phase chromatography (Biotage 40 M
  5. washeluting with a MeCH/H2O chromatography (0-60% MeCN) over 30 column volumes

Sources & evidence

ORD record
ord-3642c798797143bcaaa56727aa8b821d
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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