Sulfuric Acid → HCID 70632989, compound

HRID 1414339Notes

Reaction equation

HRID 1414339 reaction equation
[C:1]1(=[O:33])[N:5]([CH:6]2[C:26](=[O:27])[N:8]3[C:9]([C:14]([O:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)=[O:15])=[C:10]([CH3:13])[CH2:11][S:12][C@H:7]23)[C:4](=[O:28])[C:3]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:2]12.C1C[O:37]CC1.OS(O)(=O)=O.C(O)(=O)C1C(=CC=CC=1)C(N)=O>C(Cl)(Cl)Cl.CC#N.C(OCC)(=O)C.O>[C:4]([C:3]1[CH:29]=[CH:30][CH:31]=[CH:32][C:2]=1[C:1]([NH:5][CH:6]1[C:26](=[O:27])[N:8]2[C:9]([C:14]([O:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=3)=[O:15])=[C:10]([CH3:13])[CH2:11][S:12][C@H:7]12)=[O:33])([OH:28])=[O:37]

Participants

9

Reactant 4

HCID 1118Sulfuric AcidHCID 6957Phthalamic acidHCID 8028TetrahydrofuranHCID 70632848HCID 70632848, compound

Product 1

HCID 70632989HCID 70632989, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6212ChloroformSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 930 mg. (2 mmol.) of p-methoxybenzyl 7-phthalimido-3-methyl-3-cephem-4 -carboxylate in 25 ml. of THF and 8 ml. of water was cooled in an ice water bath, and 660 mg. of Na2S.9H2O were then added. The mixture was stirred for 15 min., and 10 ml. of water and 40 ml. of ethyl acetate were added. The layers were separated, and 140 mg. of a neutral material were obtained from the ethyl acetate layer. The aqueous layer was acidified to pH 4.3 with 1N H2SO4 and extracted twice with ethyl acetate. The ethyl acetate extract was washed, dried, and evaporated to give 660 mg. (68%) of the phthalamic acid as an amorphous solid, [α]D + 85.6° (MeCN); ir (CHCl3), 1781, 1740 and 1710 cm-1 ; nmr (CDCl3) δ 2.08 (s, 3, CH3), 3.1 and 3.43 (ABq, 2, J = 17 Hz), 3.79 (s, 3, CH3), 5.0 (d, 1, J = 4.5 Hz), 5.1 (s, 2, CH2), 5.8 (dd, 1, J = 4.5 Hz), 6.75-7.6 (m, 8).

Workup

  1. customThe layers were separated
  2. customof a neutral material were obtained from the ethyl acetate layer
  3. extractionextracted twice with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed
  6. customdried
  7. customevaporated
  8. customto give 660 mg

Sources & evidence

ORD record
ord-1a4390d3801c444788ed57a4250bc35c
Source dataset
uspto-grants-1977_01
Patent number
US04001239

Reaction notes

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