Acetic Acid → 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

HRID 1723391Notes

Reaction equation

HRID 1723391 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([CH:31]=[O:32])[CH:8]=[C:9]2[C:17]=1[CH:16]([CH2:18][O:19][C:20](=[O:22])[NH2:21])[C:15]1([O:24][C:25](=[O:27])[CH3:26])[O:23][N:10]2[CH2:11][CH:12]2[CH:14]1[N:13]2[C:28](=[O:30])[CH3:29])(=O)C.C(=O)(O)[O-].[Na+].C(O)(=O)C>CO>[C:25]([O:24][C:15]12[O:23][N:10]([CH2:11][CH:12]3[CH:14]1[N:13]3[C:28](=[O:30])[CH3:29])[C:9]1[C:17](=[C:5]([OH:4])[CH:6]=[C:7]([CH:31]=[O:32])[CH:8]=1)[CH:16]2[CH2:18][O:19][C:20](=[O:22])[NH2:21])(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 133974FR 66973HCID 516892Sodium Bicarbonate

Product 1

HCID 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 acetateYield 55.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 11-acetyl-8-carbamoyloxymethyl-4-formyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-6,9-diyl diacetate (52 mg) in methanol (5 ml) was added sodium bicarbonate (10 mg) in an ice-water bath. The mixture was stirred for 30 minutes in an ice-water bath and for additional 2.5 hours at ambient temperature. To the reaction mixture was added acetic acid to adjust the pH value to about 6 in an ice-water bath and the mixture was evaporated in vacuo. The residue was extracted with a mixture of chloroform and methanol (5:1, v/v) (5 ml×3). The extracts were combined and evaporated in vacuo. The residue was subjected to silica gel column chromatography and elution was carried out with a mixture of chloroform and methanol (50:1, v/v) to afford 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 (26 mg).

Workup

  1. customthe mixture was evaporated in vacuo
  2. extractionThe residue was extracted with a mixture of chloroform and methanol (5:1
  3. customevaporated in vacuo
  4. washThe residue was subjected to silica gel column chromatography and elution
  5. additionwas carried out with a mixture of chloroform and methanol (50:1

Sources & evidence

ORD record
ord-93ca82732cd34ee3b390844f32aa4ac8
Source dataset
uspto-grants-1989_08
Patent number
US04861774

Reaction notes

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