Tetrahydrofuran → HCID 70632761, compound

HRID 1730901Notes

Reaction equation

HRID 1730901 reaction equation
[C:1]1(=[O:28])[N:5]([CH:6]2[C:21](=[O:22])[N:8]3[C:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:10]([CH3:13])[CH2:11][S:12][C@H:7]23)[C:4](=[O:23])[C:3]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:2]12.[O:29]1CCCC1>O>[C:4]([C:3]1[CH:24]=[CH:25][CH:26]=[CH:27][C:2]=1[C:1]([NH:5][CH:6]1[C:21](=[O:22])[N:8]2[C:9]([C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])=[C:10]([CH3:13])[CH2:11][S:12][C@H:7]12)=[O:28])([OH:29])=[O:23]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 70633200HCID 70633200, compound

Product 1

HCID 70632761HCID 70632761, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 800 mg. (2 mmol.) of t-butyl 7-phthalimido-3-methyl-3-cephem-4-carboxylate in 25 ml. of tetrahydrofuran and 8 ml. of water was cooled in an ice bath. To the solution 660 mg. of Na2S.9H2O were added, and the mixture was stirred and cooled for 10 min. At the end of this period 10 ml. of water were added, and the mixture was extracted with 40 ml. of ethyl acetate. The extract was discarded. The aqueous portion was acidified to pH 4.3 with 1N H2SO4 and then extracted with ethyl acetate. The ethyl acetate extract was dried and evaporated, giving 700 mg. of the title compound. The product was recrystallized from chloroform/cyclohexane; m.p. 178°-179°; ir (nujol) 1770, 1735, and 1680 cm-1 ; nmr (CDCl3 + DMSOd6) δ 1.5 (s, 9, t-Bu), 2.1 (s, 3, CH3), 3.2 and 3.5 (ABq, 2, J = 18 Hz), 5.02 (d, 1, J = 4.5 Hz), 5.82 (dd, 1, J = 4.5 and 9Hz), and 7.4-8 (m, H, ArH).

Workup

  1. temperaturecooled for 10 min
  2. extractionthe mixture was extracted with 40 ml
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. customwas dried
  6. customevaporated
  7. customgiving 700 mg

Sources & evidence

ORD record
ord-1874eae7ad034cdbaf25ed9f5407c39c
Source dataset
uspto-grants-1976_11
Patent number
US03994888

Reaction notes

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