Acetic Anhydride → 4-Acetoxymethyl-11-acetyl-8-carbamoyloxymethyl-9-hydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-trien-6-yl acetate

HRID 1723364Notes

Reaction equation

HRID 1723364 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]([CH2:20][OH:21])[CH:10]=2)[NH2:2].C(O[C:28](=[O:30])[CH3:29])(=O)C>N1C=CC=CC=1>[C:4]([O:22][C:7]1[CH:8]=[C:9]([CH2:20][O:21][C:28](=[O:30])[CH3:29])[CH:10]=[C:11]2[C:6]=1[CH:5]([CH2:4][O:3][C:1](=[O:23])[NH2:2])[C:17]1([OH:19])[O:18][N:12]2[CH2:13][CH:14]2[CH:16]1[N:15]2[C:17](=[O:18])[CH3:16])(=[O:3])[CH3:5]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 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

Product 1

HCID 150517214-Acetoxymethyl-11-acetyl-8-carbamoyloxymethyl-9-hydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-trien-6-yl acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 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 (21 mg) in pyridine (1 ml) was added acetic anhydride (34 μl), and the mixture was allowed to stand at room temperature overnight. The reaction mixture was evaporated to dryness in vacuo, and the residual oil was subjected to preparative thin layer chromatography, which was developed with a mixture of methanol and chlorform (5:95, v/v) to give 4-acetoxymethyl-11-acetyl-8-carbamoyloxymethyl-9-hydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-6-yl acetate (24 mg).

Workup

  1. customThe reaction mixture was evaporated to dryness in vacuo
  2. additionwas developed with a mixture of methanol and chlorform (5:95

Sources & evidence

ORD record
ord-e5b91f66bb6c4931a4c2d1c060222610
Source dataset
uspto-grants-1989_08
Patent number
US04861774

Reaction notes

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