Sodium borohydride → (7,9-Dihydroxy-5-(hydroxymethyl)-1,1a,2,8,9,9a-hexahydro-3,9-epoxyazireno(2,3-c)(1)benzazocin-8-yl)methyl hydrogen carbonimidate

HRID 1723369Notes

Reaction equation

HRID 1723369 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].[BH4-].[Na+]>CO>[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]([CH2:20][OH:21])[CH:10]=2)[NH2:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 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 124136(7,9-Dihydroxy-5-(hydroxymethyl)-1,1a,2,8,9,9a-hexahydro-3,9-epoxyazireno(2,3-c)(1)benzazocin-8-yl)methyl hydrogen carbonimidate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 (30 mg) in methanol (3 ml) was added sodium borohydride (40 mg), and the mixture was stirred at room temperature for 1 hour. After evaporation of the solvent, the residue was subjected to column chromatography on non-ionic adsorption resin "Diaion HP-20" (Trade Mark, maker Mitsubishi Chemical Industries Ltd.). Elution was carried out with 50% methanol, and fractions containing the desired compound were collected. The solvent was evaporated off to give 6,9-dihydroxy-4-hydroxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-8-ylmethyl carbamate, which was dissolved in pyridine (1 ml). To this solution was added acetic anhydride (0.5 ml), and the resultant solution was allowed to stand at room temperature overnight. Removal of the solvent by using high vacuum pump gave an oil, 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 4-acetoxymethyl-11-acetyl-8-carbamoyloxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-6,9-diyl diacetate (12 mg).

Workup

  1. customAfter evaporation of the solvent
  2. washElution
  3. additioncontaining the desired compound
  4. customwere collected
  5. customThe solvent was evaporated off

Sources & evidence

ORD record
ord-fccf50c20e7f402c9e9d505b5cb979dd
Source dataset
uspto-grants-1989_08
Patent number
US04861774

Reaction notes

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