Methanol → HCID 15051716, compound

HRID 236579Notes

Reaction equation

HRID 236579 reaction equation
[C:1](=[O:23])([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:22])[CH:8]=[C:9]([CH:20]=[O:21])[CH:10]=2)[NH2:2].[C:24](OC(=O)C)(=[O:26])[CH3:25].[CH:31](Cl)(Cl)Cl.[CH3:35][OH:36]>>[C:35]([O:22][C:7]1[CH:8]=[C:9]([CH:20]=[O:21])[CH:10]=[C:11]2[C:6]=1[CH:5]([CH2:4][O:3][C:1](=[O:23])[NH2:2])[C:17]1([OH:19])[O:18][N:12]2[CH2:13][CH:14]2[CH:16]1[N:15]2[C:24](=[O:26])[CH3:25])(=[O:36])[CH3:31]

Participants

5

Reactant 4

HCID 887Methanol2×HCID 6212ChloroformHCID 7918Acetic AnhydrideHCID 10448726(4-Formyl-6,9-dihydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2(7),3,5-trien-8-yl)methyl carbamate

Product 1

HCID 15051716HCID 15051716, compound

Procedure

To a solution of 4-formyl-6,9-dihydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-8-ylmethyl carbamate (20 mg) in methanol (2 ml) was added acetic anhydride (1 ml), and the mixture was stirred at room temperature for 1 hour. The solvent and the excess of acetic anhydride was removed in vacuo to give a residue, which was subjected to preparative thin layer chromatography. Development was carried out with a mixture of methanol and chloroform (1:9, v/v) to afford 11-acetyl-8-carbamoyloxymethyl-4-formyl-9-hydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-6-yl acetate (9 mg).

Workup

  1. customThe solvent and the excess of acetic anhydride was removed in vacuo
  2. customto give a residue, which

Sources & evidence

ORD record
ord-86dd8870b6304195973c2e670eb25103
Source dataset
uspto-grants-1987_02
Patent number
US04645765

Reaction notes

Loading…