Water → 6,9-Diacetoxy-8-carbamoyloxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-triene-4-carboxylic acid

HRID 1252437Notes

Reaction equation

HRID 1252437 reaction equation
[C:1]([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]2C(=O)C)(=[O:3])[CH3:2].O.S(=O)(=O)(O)[OH:35].C(O)(C)C>CC(C)=O.[O-2].[O-2].[O-2].[Cr+6]>[C:1]([O:4][C:5]1[CH:6]=[C:7]([C:31]([OH:35])=[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[NH:13]2)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 962Water2×HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 133974FR 66973

Product 1

HCID 150517396,9-Diacetoxy-8-carbamoyloxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-triene-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

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 (29 mg) in acetone (2 ml) was added a mixture of chromium trioxide (26 mg), water (76 μl) and sulfuric acid (22 μl) in an ice-water bath. After stirring for 30 minutes in an ice-water bath, isopropyl alcohol (2 ml) was added to the reaction mixture. The resultant mixture was then poured into water (10 ml) and extracted with a mixture of chloroform and methanol (2:1, v/v) (10 ml×5). The extracts were combined and dried over magnesium sulfate, and then evaporated in vacuo. The residue was subjected to preparative thin layer chromatography, which was developed with a mixture of chloroform, methanol and water (65:25:4, v/v) to afford 6,9-diacetoxy-8-carbamoyloxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-triene-4-carboxylic acid (5 mg).

Workup

  1. extractionextracted with a mixture of chloroform and methanol (2:1
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. additionwas developed with a mixture of chloroform, methanol and water (65:25:4, v/v)

Sources & evidence

ORD record
ord-78c0f76d74024a2a98ffd7efdbd5dba8
Source dataset
uspto-grants-1988_05
Patent number
US04743555

Reaction notes

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