Sodium Hydroxide → HCID 66770098, compound

HRID 2044014Notes

Reaction equation

HRID 2044014 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-4540cb183cb148e8851fdf2ad9afed67
Source dataset
uspto-grants-2013_11
Patent number
US08586744B2

Reaction notes

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