Sodium Hydroxide → HCID 66770098, compound

HRID 1188730Notes

Reaction equation

HRID 1188730 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][P:6]([C:11]1([NH:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:13][CH:12]1[CH:14]=[CH2:15])([O:8][CH2:9][CH3:10])=[O:7])C.[OH-].[Na+]>C1COCC1>[CH2:20]([O:19][C:17]([NH:16][C:11]1([P:6]([CH2:5][C:4]([OH:27])=[O:3])([O:8][CH2:9][CH3:10])=[O:7])[CH2:13][CH:12]1[CH:14]=[CH2:15])=[O:18])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66769938HCID 66769938, compound

Product 1

HCID 66770098HCID 66770098, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [(1-benzyloxycarbonylamino-2-vinyl-cyclopropyl)-ethoxy-phosphinoyl]-acetic acid ethyl ester (352 mg, 0.89 mmol) in THF (3 mL) was stirred at 0° C. as 1 N NaOH (980 μL, 0.98 mmol) was added. The solution was stirred overnight at r.t. and then concentrated, diluted with H2O (10 mL) and washed with ethyl acetate. The aqueous layer was acidified with 1 N HCl (5 mL) and extracted with ethyl acetate (×2). The organic extracts were washed with H2O, dried (MgSO4) and concentrated to yield [(1-Benzyloxycarbonylamino-2-vinyl-cyclopropyl)-ethoxy-phosphinoyl]-acetic acid (224 mg, 69%). 1H NMR (300 MHz, CDCl3): d 7.34 (s, 5H), 5.91 (m, 2H), 5.20 (m, 2H), 4.21 (m, 2H), 3.11 (m, 2H), 2.30 (m, 1H), 2.03 (m, 1H), 1.85 (m, 2H), 1.70 (m, 2H), 1.58 (m, 2H), 1.38 (m, 2H), 1.25 (m, 3H). 31P (121.4 MHz, CDCl3): 45.109, 41.119, 40.965, 39.514

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. additiondiluted with H2O (10 mL)
  4. washwashed with ethyl acetate
  5. extractionextracted with ethyl acetate (×2)
  6. washThe organic extracts were washed with H2O
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-16a33bdd66864cd8bd6a466496682a69
Source dataset
uspto-grants-2014_03
Patent number
US08674088B2

Reaction notes

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