Hydrochloric Acid → [2-Hydroxy-3-methyl-1-(3-oxo-propylcarbamoyl)-butyl]-carbamic acid benzyl ester

HRID 25689Notes

Reaction equation

HRID 25689 reaction equation
[CH2:1]([O:8][C:9](=[O:29])[NH:10][CH:11]([C:17](=[O:28])[NH:18][CH2:19][CH2:20][CH:21](OCC)[O:22]CC)[CH:12]([OH:16])[CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9](=[O:29])[NH:10][CH:11]([C:17](=[O:28])[NH:18][CH2:19][CH2:20][CH:21]=[O:22])[CH:12]([OH:16])[CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 69753234[1-(3,3-Diethoxy-propylcarbamoyl)-2-hydroxy-3-methyl-butyl]-carbamic acid benzyl ester

Product 1

HCID 20759880[2-Hydroxy-3-methyl-1-(3-oxo-propylcarbamoyl)-butyl]-carbamic acid benzyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [1-(3,3-diethoxy-propylcarbamoyl)-2-hydroxy-3-methyl-butyl]-carbamic acid benzyl ester (350 mg, 0.854 mmol) in anhydrous tetrahydrofuran (2 ml) was added 0.5N hydrochloric acid (2 ml). The resulting solution was stirred for 20 minutes at room temperature. The aqueous layer was basified to pH 8 with sodium bicarbonate solution, and extracted with ethyl acetate (3×40 mL). The combined extracts were washed with saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated in vacuo to provide [2-hydroxy-3-methyl-1-(3-oxo-propylcarbamoyl)-butyl]-carbamic acid benzyl ester (266 mg, 93%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate (3×40 mL)
  2. washThe combined extracts were washed with saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-828417c7354d44b6bb9f49be89dc6640
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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