HCID 86741322, compound → HCID 53702619, compound

HRID 1723393Notes

Reaction equation

HRID 1723393 reaction equation
[C:1](=[O:25])([O:3][CH2:4][CH:5]1[C:17]2([OH:19])[O:18][N:12]([CH2:13][CH:14]3[CH:16]2[NH:15]3)[C:11]2[C:6]1=[C:7]([OH:24])[CH:8]=[C:9]([CH:20]=[N:21][O:22][CH3:23])[CH:10]=2)[NH2:2]>N1C=CC=CC=1.C(OC(=O)C)(=O)C>[C:4]([O:24][C:7]1[CH:8]=[C:9]([CH:20]=[N:21][O:22][CH3:23])[CH:10]=[C:11]2[C:6]=1[CH:5]([CH2:4][O:3][C:1](=[O:25])[NH2:2])[C:17]1([O:19][C:17](=[O:18])[CH3:16])[O:18][N:12]2[CH2:13][CH:14]2[CH:16]1[N:15]2[C:7](=[O:24])[CH3:6])(=[O:3])[CH3:5]

Participants

4

Reactant 1

HCID 86741322HCID 86741322, compound

Product 1

HCID 53702619HCID 53702619, compoundYield 165.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 7918Acetic AnhydrideSolvent

Procedure

6,9-Dihydroxy-4-methoxyiminomethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-8-ylmethyl carbamate (55 mg) was dissolved in a mixture of pyridine (3 ml) and acetic anhydride (1.5 ml) and stirred for 12 hours at ambient temperature. The mixture was evaporated in vacuo and subjected to preparative thin layer chromatography, which was developed with a mixture of chloroform and methanol (20:1, v/v) to afford 11-acetyl-8-carbamoyloxymethyl-4-methoxyiminomethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-6,9-diyl diacetate (62 mg).

Workup

  1. customThe mixture was evaporated in vacuo
  2. additionwas developed with a mixture of chloroform and methanol (20:1

Sources & evidence

ORD record
ord-f50e000dbcfb4cdebb32b2850c7788f2
Source dataset
uspto-grants-1989_08
Patent number
US04861774

Reaction notes

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