Hydrochloric Acid → HCID 59710970, compound

HRID 2221440Notes

Reaction equation

HRID 2221440 reaction equation
[C:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:17][CH:18]=[C:19]([C:21]([O:23]C)=[O:22])[N:20]=2)=[CH:12][CH:11]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CO.[Li+].[OH-].Cl>C1COCC1>[C:1]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[O:17][CH:18]=[C:19]([C:21]([OH:23])=[O:22])[N:20]=2)=[CH:14][CH:15]=1)([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 69201725HCID 69201725, compound

Product 1

HCID 59710970HCID 59710970, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-[4-(N-Boc-aminomethyl)-phenyl]-oxazol-4-ylcarboxylate (1.66 g, 5 mmol) in THF (25 ml)/methanol (25 ml) was added 1M aqueous LiOH (25 ml, 25 mmol). After stirring at room temperature for 3 h, the solution was acidified with 2M aqueous HCl to pH 5-6, and partitioned between ethyl acetate (150 ml) and water (150 ml). The organic layer was washed with brine (150 ml), dried over sodium sulfate and concentrated in vacuo giving the title compound as a white solid (1.58 g, 4.96 mmol).

Workup

  1. custompartitioned between ethyl acetate (150 ml) and water (150 ml)
  2. washThe organic layer was washed with brine (150 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8bec33af51e49d3bc47ab8ed416ecfb
Source dataset
uspto-grants-2008_05
Patent number
US07368572B2

Reaction notes

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