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Hydrochloric Acid → 6,9-Dihydroxy-8-methylene-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-triene-4-carbaldehyde

HRID 1252427
Notes
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Reaction equation

HRID 1252427 reaction equation
C(=O)(O[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)N.Cl>[OH-].[Na+]>[OH:22][C:7]1[CH:8]=[C:9]([CH:20]=[O:21])[CH:10]=[C:11]2[C:6]=1[C:5](=[CH2:4])[C:17]1([OH:19])[O:18][N:12]2[CH2:13][CH:14]2[CH:16]1[NH:15]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 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 150517286,9-Dihydroxy-8-methylene-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-triene-4-carbaldehydeYield 71%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

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 (40 mg) was dissolved in 1N aqueous sodium hydroxide (4 ml) and the solution was heated at 50° C. for 100 minutes under argon atmosphere. The reaction mixture was cooled and neutralized with 1N aqueous hydrochloric acid (4 ml) and the resultant aqueous solution was lyophilized. The residue was subjected to a silica gel column chromatography and elution was carried out with a mixture of methanol and chloroform (1:4, v/v). The desired fractions were combined and then evaporated to dryness in vacuo to give 6,9-dihydroxy-8-methylene-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-triene-4-carbaldehyde (23 mg).

Workup

  1. temperatureThe reaction mixture was cooled
  2. washThe residue was subjected to a silica gel column chromatography and elution
  3. additionwas carried out with a mixture of methanol and chloroform (1:4, v/v)
  4. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-6814a658f66b40db8620dfb2d53e86df
Source dataset
uspto-grants-1988_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04743555

Reaction notes

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