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 236587Notes

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

Participants

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

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

Sources & evidence

ORD record: ord-182a21ff5dbc43f38e243d48317305bd
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04645765

Reaction notes

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