Acetic Anhydride → HCID 15051750, compound

HRID 236604Notes

Reaction equation

HRID 236604 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:19]=[O:20])[CH:5]=[C:6]2[C:14]=1[CH:13]([CH2:15][OH:16])[C:12]1([OH:18])[O:17][N:7]2[CH2:8][CH:9]2[CH:11]1[NH:10]2.[C:21](OC(=O)C)(=[O:23])[CH3:22]>CO>[C:21]([N:10]1[CH:9]2[CH:11]1[C:12]1([OH:18])[O:17][N:7]([CH2:8]2)[C:6]2[C:14](=[C:2]([OH:1])[CH:3]=[C:4]([CH:19]=[O:20])[CH:5]=2)[CH:13]1[CH2:15][OH:16])(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15051730HCID 15051730, compound

Product 1

HCID 15051750HCID 15051750, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6,9-dihydroxy-8-hydroxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-triene-4-carbaldehyde (98 mg) in methanol (3 ml) was added acetic anhydride (40 μl). The mixture was stirred for 1 hour at ambient temperature and evaporated in vacuo. The residue was subjected to preparative thin layer chromotography, which was developed with a mixture of chloroform and methanol (10:1, v/v) to afford 11-acetyl-6,9-dihydroxy-8-hydroxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-triene-4-carbaldehyde (71 mg).

Workup

  1. customevaporated in vacuo
  2. additionwas developed with a mixture of chloroform and methanol (10:1

Sources & evidence

ORD record
ord-bdf6897252b249fca7d4447d9b072f89
Source dataset
uspto-grants-1987_02
Patent number
US04645765

Reaction notes

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