Hydrochloric Acid → HCID 86587224, compound

HRID 2414692Notes

Reaction equation

HRID 2414692 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C@@H:12]([NH:19]C(OC(C)(C)C)=O)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8][CH:7]=1)[CH:2]([CH3:4])[CH3:3].Cl>C(OCC)(=O)C>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C@@H:12]([NH2:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8][CH:7]=1)[CH:2]([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69818093HCID 69818093, compound

Product 1

HCID 86587224HCID 86587224, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of ethyl 3-(4-isobutyloxyphenyl)-3-(S)-tert-butyloxycarbonylamino-propionate (0.42 g) in ethyl acetate (5 ml) was added 4N hydrogen chloride in ethyl acetate (5 ml) at 0° C. After stirring for 2.5 hours at ambient temperature, the mixture was partitioned between a mixture of ethyl acetate and a saturated aqueous NaHCO3 solution. The separated organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by a silica gel column chromatography eluting with chloroform and methanol (19:1 to 4:1) to give ethyl 3-(4-isobutyloxyphenyl)-3-(S)-amino-propionate(100 mg, 33.7%).

Workup

  1. customthe mixture was partitioned between a mixture of ethyl acetate
  2. washThe separated organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column chromatography
  6. washeluting with chloroform and methanol (19:1 to 4:1)

Sources & evidence

ORD record
ord-e714b246ab8a4c029bc150cb18d8c90d
Source dataset
uspto-grants-2004_11
Patent number
US06812235B2

Reaction notes

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