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 236581Notes

Reaction equation

HRID 236581 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 chloroform (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 chloroform (5:95

Sources & evidence

ORD record
ord-71cebb2e9c4b4cfdaf65ccc9e20ad374
Source dataset
uspto-grants-1987_02
Patent number
US04645765

Reaction notes

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