Sodium Bicarbonate → HCID 131733526, compound

HRID 2283687Notes

Reaction equation

HRID 2283687 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:13]([O:15][CH2:16][C@H:17]1[C@H:21]([CH3:22])[O:20]C(C)(C)[N:18]1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH3:14].C(=O)(O)[O-].[Na+]>CO>[C:28]([O:27][C:25](=[O:26])[NH:18][C@H:17]([C@@H:21]([OH:20])[CH3:22])[CH2:16][O:15][CH2:13][CH3:14])([CH3:29])([CH3:30])[CH3:31]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 90308911HCID 90308911, compound

Product 1

HCID 131733526HCID 131733526, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methanol (130 mL) and p-toluenesulfonic acid monohydrate (134 mg) were added to (4S,5S)-tert-butyl 4-(ethoxymethyl)-2,2,5-trimethyloxazolidine-3-carboxylate obtained in the above-described Step 1 (1.34 g), and the reaction solution was stirred at room temperature overnight. An aqueous sodium bicarbonate solution was added to the reaction solution, and methanol was evaporated under vacuum. Water and ethyl acetate were added, the organic layer was separated, and then washed with a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain tert-butyl((2S,3S)-1-ethoxy-3-hydroxybutan-2-yl)carbamate as colorless amorphous.

Workup

  1. customobtained in the above-described Step 1 (1.34 g)
  2. customwas evaporated under vacuum
  3. additionWater and ethyl acetate were added
  4. customthe organic layer was separated
  5. washwashed with a saturated saline solution
  6. dry with materialAfter drying over anhydrous sodium sulfate
  7. customthe solvent was evaporated under vacuum
  8. customThe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1cedd6fe7bf84a668891d1ca6e7b0cb4
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

Loading…