Water → HCID 68801930, compound

HRID 2222960Notes

Reaction equation

HRID 2222960 reaction equation
C([O:3][C:4](=[O:24])[C@@H:5]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[O:14][CH:13]=[N:12][C:11]=2[CH:15]=1)C.O.O.[OH-].[Li+]>O1CCCC1.[Cl-].[Na+].O>[O:14]1[C:10]2[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:4]([OH:24])=[O:3])=[CH:15][C:11]=2[N:12]=[CH:13]1

Participants

6

Reactant 3

HCID 962Water2×HCID 168937Lithium hydroxide, monohydrateHCID 68800773HCID 68800773, compound

Product 1

HCID 68801930HCID 68801930, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (S)-3-benzooxazol-5-yl-2-tert-butoxycarbonylamino-propionic acid ethyl ester (0.54 g, 1.61 mmol) in tetrahydrofuran (10 mL) was added water (5 mL) and lithium hydroxide monohydrate (111 mg, 2.65 mmol) and the mixture stirred at ambient temperature under argon for 1 hour. The reaction mixture was poured into water (50 mL), diluted with brine (25 mL) and extracted with ethyl acetate (3×25 mL). The combined organic extracts were washed with brine (50 mL), dried over sodium sulfate and concentrated in vacuo to give crude (S)-3-benzooxazol-5-yl-2-tert-butoxycarbonylamino-propionic acid an off white solid foam which was used without further purification (0.49 g, 99%).

Workup

  1. extractionextracted with ethyl acetate (3×25 mL)
  2. washThe combined organic extracts were washed with brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4d81b8e37a1d4ee8aeddd1a5896c16e7
Source dataset
uspto-grants-2008_05
Patent number
US07371869B2

Reaction notes

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