Hydrochloric Acid → HCID 12084902, compound

HRID 1795485Notes

Reaction equation

HRID 1795485 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2(O)[O:19]C[N:17]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[C@H:16]2[CH:30]([CH3:32])[CH3:31])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.Cl>O1CCCC1.C1(C)C=CC=CC=1>[CH2:23]([O:22][C:20]([NH:17][C@@H:16]([CH:30]([CH3:32])[CH3:31])[C:15]([C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)=[O:19])=[O:21])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 12084901HCID 12084901, compound

Product 1

HCID 12084902HCID 12084902, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (4 mL) was dissolved (4S)-N-benzyloxycarbonyl-5-(4-benzyloxyphenyl)-4-isopropyl-5-hydroxyoxazolidine (1.38 g) prepared in Example 8, and to the solution were added water (5 mL) and conc. hydrochloric acid (2 mL). The mixture was stirred at room temperature for 24 hours. The reaction was diluted with toluene and the aqueous layer was discarded. The organic layer was washed with water three times. The organic layer was dried over anhydrous magnesium sulfate and then concentrated in vacuo. The residue was purified by silica column chromatography (eluent: hexane/ethyl acetate=2/1) to give the title compound (466 mg) as pale yellow crystals in a yield of 36%.

Workup

  1. washThe organic layer was washed with water three times
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica column chromatography (eluent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-6d7d88bcae154fe885eb44cda27800c3
Source dataset
uspto-grants-2006_04
Patent number
US07026515B2

Reaction notes

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