Chloroform → 11-Acetyl-6-butoxy-8-carbamoyloxymethyl-4-formyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-trien-9-yl acetate

HRID 1723398Notes

Reaction equation

HRID 1723398 reaction equation
[C:1]([O:4][C:5]12[O:21][N:13]([CH2:14][CH:15]3[CH:17]1[N:16]3[C:18](=[O:20])[CH3:19])[C:12]1[C:7](=[C:8]([OH:24])[CH:9]=[C:10]([CH:22]=[O:23])[CH:11]=1)[CH:6]2[CH2:25][O:26][C:27](=[O:29])[NH2:28])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:36](I)[CH2:37][CH2:38][CH3:39].C(Cl)(Cl)Cl>CC(C)=O.CO>[C:1]([O:4][C:5]12[O:21][N:13]([CH2:14][CH:15]3[CH:17]1[N:16]3[C:18](=[O:20])[CH3:19])[C:12]1[C:7](=[C:8]([O:24][CH2:36][CH2:37][CH2:38][CH3:39])[CH:9]=[C:10]([CH:22]=[O:23])[CH:11]=1)[CH:6]2[CH2:25][O:26][C:27](=[O:29])[NH2:28])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 984418511-Acetyl-8-carbamoyloxymethyl-4-formyl-6-hydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-trien-9-yl acetate

Product 1

HCID 5419058611-Acetyl-6-butoxy-8-carbamoyloxymethyl-4-formyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-trien-9-yl acetate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 11-acetyl-8-carbamoyloxymethyl-4-formyl-6-hydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-9-yl acetate (80 mg) in acetone (1 ml) were added potassium carbonate (110 mg) and n-butyl iodide (90 μl), and the mixture was stirred at 50° C. for 4 hours. The reaction mixture was subjected to preparative thin layer chromatography, which was developed with a mixture of chloroform and methanol (20:1, v/v) to afford 11-acetyl-6-butoxy-8-carbamoyloxymethyl-4-formyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-9-yl acetate (61 mg).

Sources & evidence

ORD record
ord-141c8f74aaef4e549fbe26af2436e0d9
Source dataset
uspto-grants-1989_08
Patent number
US04861774

Reaction notes

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