p-Toluenesulfonic acid → HCID 15051746, compound

HRID 236601Notes

Reaction equation

HRID 236601 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:27](OC)[O:28]C)[CH:8]=[C:9]2[C:17]=1[C:16](=[O:18])[C:15]1([O:20][C:21](=[O:23])[CH3:22])[O:19][N:10]2[CH2:11][CH:12]2[CH:14]1[N:13]2C(=O)C)(=[O:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(Cl)(Cl)Cl>CC(C)=O>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:27]=[O:28])[CH:8]=[C:9]2[C:17]=1[C:16](=[O:18])[C:15]1([O:20][C:21](=[O:23])[CH3:22])[O:19][N:10]2[CH2:11][CH:12]2[CH:14]1[NH:13]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6212ChloroformHCID 15051745HCID 15051745, compound

Product 1

HCID 15051746HCID 15051746, compoundYield 20.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of A-isomer of 11-acetyl-4-dimethoxymethyl-8-oxo-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-6,9-diyl diacetate (6 mg) in acetone (0.5 ml) was added p-toluene sulfonic acid (1 mg). The mixture was stirred for 1 hour at ambient temperature, and then subjected to preparative thin layer chromatography, which was developed with a mixture of chloroform and acetone (5:1, v/v) to afford A-isomer of 4-formyl-8-oxo-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-6,9-diyl diacetate (1 mg).

Sources & evidence

ORD record
ord-074ac639c5f54f14b4b0794949d241a0
Source dataset
uspto-grants-1987_02
Patent number
US04645765

Reaction notes

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