Hydrochloric Acid → HCID 58909201, compound

HRID 1295612Notes

Reaction equation

HRID 1295612 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[CH:15]=[CH:14][O:13][C:12]=1[NH:16][C:17](=[O:23])OC(C)(C)C)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:25](Cl)(=O)[CH2:26][CH2:27]C>>[CH2:1]([NH:8][C:9]([C:11]1[CH:15]=[CH:14][O:13][C:12]=1[NH:16][C:17](=[O:23])[CH2:25][CH2:26][CH3:27])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8855Butyryl chlorideHCID 58909210HCID 58909210, compound

Product 1

HCID 58909201HCID 58909201, compound

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl 3-[(benzylamino)carbonyl]-2-furylcarbamate (1-1, 1 equiv) is saturated with HCl gas at 0° C., and the resulting solution is stirred at 0° C. for 1 h, then allowed to warm to 23° C. and stirred for 1 h. The reaction mixture is concentrated and the residue is dissolved in pyridine. The resulting solution is cooled to 0° C., and butyryl chloride (3 equiv) is added in three equal portions over 1 h. The reaction mixture is partitioned between aqueous sodium bicarbonate solution and ethyl acetate. The organic layer is dried over sodium sulfate and concentrated. The residue is purified by flash column (hexanes initially, grading to 100% ethyl acetate) to give N-benzyl-2-(butyrylamino)-3-furamide (1-2).

Workup

  1. temperatureto warm to 23° C.
  2. stirringstirred for 1 h
  3. concentrationThe reaction mixture is concentrated
  4. dissolutionthe residue is dissolved in pyridine
  5. temperatureThe resulting solution is cooled to 0° C.
  6. customThe reaction mixture is partitioned between aqueous sodium bicarbonate solution and ethyl acetate
  7. dry with materialThe organic layer is dried over sodium sulfate
  8. concentrationconcentrated
  9. customThe residue is purified by flash column (hexanes initially

Sources & evidence

ORD record
ord-914c15b988424f0596f7ded3b01e3650
Source dataset
uspto-grants-2007_07
Patent number
US07244723B2

Reaction notes

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