Water → t-Butyl 7-(2-carboxybenzamido)-3-acetoxymethyl-3-cephem-4-carboxylate

HRID 1730899Notes

Reaction equation

HRID 1730899 reaction equation
[C:1]1(=[O:32])[N:5]([CH:6]2[C:25](=[O:26])[N:8]3[C:9]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[C:10]([CH2:13][O:14][C:15](=[O:17])[CH3:16])[CH2:11][S:12][C@H:7]23)[C:4](=[O:27])[C:3]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:2]12.C1C[O:36]CC1.[OH-].[Na+].O>C(OCC)(=O)C>[C:1]([C:2]1[CH:31]=[CH:30][CH:29]=[CH:28][C:3]=1[C:4]([NH:5][CH:6]1[C:25](=[O:26])[N:8]2[C:9]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])=[C:10]([CH2:13][O:14][C:15](=[O:17])[CH3:16])[CH2:11][S:12][C@H:7]12)=[O:27])([OH:36])=[O:32]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 70633201t-Butyl 7-phthalimido-3-acetoxymethyl-3-cephem-4-carboxylate

Product 1

HCID 70633183t-Butyl 7-(2-carboxybenzamido)-3-acetoxymethyl-3-cephem-4-carboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 458 mg. (1 mmol.) of t-butyl 7-phthalimido-3-acetoxymethyl-3-cephem-4-carboxylate in 10 ml. of THF was cooled in an ice water bath, and 1.1 ml. of 1N NaOH were then added. After stirring for 5 min., 10 ml. of water and 30 ml. of ethyl acetate were added. The ethyl acetate layer was separated, and 70 mg. of starting material were recovered therefrom. The aqueous layer was acidified to pH 4.0, and the acidified layer was extracted with ethyl acetate. After workup, 330 mg. (83%) of the desired phthalamic acid were obtained [α] + 26.37 (MeCN); λEtOH 260 mμ (ε 8800)D ; ir (CHCl3) 1785, 1730 and 1685 cm-1 ; nmr (CDCl3) δ 1.55 (s, 9, t-Bu), 2.05 (s, 3, Ac), 3.3 and 3.6 (ABq, 2, J = 17 Hz), 4.72 and 5.2 (ABq, 2, J = 14 Hz), 4.98 (d, 1, J = 4.5 Hz), 5.9 (dd, 1, J = 4.5 and 9 Hz), and 7.5-8 (m, 4, ArH).

Workup

  1. customThe ethyl acetate layer was separated
  2. customof starting material were recovered
  3. extractionthe acidified layer was extracted with ethyl acetate

Sources & evidence

ORD record
ord-3534a5ecf36b4c9e974983d57d43fb99
Source dataset
uspto-grants-1976_11
Patent number
US03994888

Reaction notes

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