Water → HCID 70173263, compound

HRID 1532783Notes

Reaction equation

HRID 1532783 reaction equation
[C:1]([N:8]1[C:12]([C:13]([O:15]C)=[O:14])=[CH:11][O:10][CH:9]1[C@H:17]([NH2:26])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(=O)([O-])[O-].[K+].[K+].O>CO.O>[C:1]([N:8]1[C:12]([C:13]([OH:15])=[O:14])=[CH:11][O:10][CH:9]1[C@H:17]([NH2:26])[CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 70178254HCID 70178254, compound

Product 1

HCID 70173263HCID 70173263, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of methyl N-Boc-2-[(1R)-1-amino-3-phenylpropyl]4-oxazolecarboxylate (388 mg) and potassium carbonate (1.5 g) in 90% methanol/water (10 mL) is brought to gentle reflux for 40 min. The reaction mixture is cooled, water is added and extracted thrice with ethyl acetate. The aqueous layer is acidified to pH 3 and extracted three times with ethyl acetate. The combined organic layer is washed twice with brine, dried (Na2SO4) and concentrated. The crude title product (372 mg) was >95% pure by NMR: 1H NMR (400 MHz, CDCl3) δ1.41 (s, 9H), 2.18 (m, 1H), 2.22 (m, 1H), 2.69 (m, 2H), 5.01 (m, 1H), 5.88 (bs, 1H, NH), 7.16 (m, 3H), 7.23 (m, 2H), and 8.01 (s, 1H).

Workup

  1. temperatureto gentle reflux for 40 min
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted thrice with ethyl acetate
  4. extractionextracted three times with ethyl acetate
  5. washThe combined organic layer is washed twice with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b95abe2cd2b74f91863e33efcabc7408
Source dataset
uspto-grants-2001_03
Patent number
US06204279B1

Reaction notes

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