Acetic Acid → HCID 15051752, compound

HRID 236608Notes

Reaction equation

HRID 236608 reaction equation
[H-].[Na+].[C:3]([O:6][C:7]1[CH:8]=[C:9]([CH:30]([O:33][CH3:34])[O:31][CH3:32])[CH:10]=[C:11]2[C:19]=1[CH:18]([CH2:20][O:21][C:22](=[O:24])[NH2:23])[C:17]1([O:26][C:27](=[O:29])[CH3:28])[O:25][N:12]2[CH2:13][CH:14]2[CH:16]1[NH:15]2)(=[O:5])[CH3:4].CI.[C:37](O)(=O)C>O1CCCC1>[C:3]([O:6][C:7]1[CH:8]=[C:9]([CH:30]([O:31][CH3:32])[O:33][CH3:34])[CH:10]=[C:11]2[C:19]=1[CH:18]([CH2:20][O:21][C:22](=[O:24])[NH2:23])[C:17]1([O:26][C:27](=[O:29])[CH3:28])[O:25][N:12]2[CH2:13][CH:14]2[CH:16]1[N:15]2[CH3:37])(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15051737HCID 15051737, compound

Product 1

HCID 15051752HCID 15051752, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (60% in oil, 4 mg) in tetrahydrofuran (0.5 ml) was added a solution of B-isomer of 8-carbamoyloxymethyl-4-dimethoxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-6,9-diyl diacetate (20 mg) in tetrahydrofuran (2.0 mg) in an ice-water bath. To this solution was added methyl iodide (0.4 ml) in an ice-water bath. After stirring for 3 hours at ambient temperature, acetic acid (0.1 ml) was added to the reaction mixture in an ice-water bath. The resultant mixture was evaporated in vacuo and the residual oil was subjected to preparative thin layer chromatography, which was developed with a mixture of chloroform and methanol (8:1, v/v) to afford 8-carbamoyloxymethyl-4-dimethoxymethyl-11-methyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-6,9-diyl diacetate (11 mg).

Workup

  1. customThe resultant mixture was evaporated in vacuo
  2. additionwas developed with a mixture of chloroform and methanol (8:1

Sources & evidence

ORD record
ord-90c5466f1c7b4d54a27afe456271d73d
Source dataset
uspto-grants-1987_02
Patent number
US04645765

Reaction notes

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