Putrescine → HCID 13577176, compound

HRID 746161Notes

Reaction equation

HRID 746161 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].[C:7]([C@:10]1([OH:21])C(=O)[O:14][C:12](=[O:13])[C@:11]1(C(=O)C)[OH:17])(=[O:9])C>O1CCCC1>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:9])[CH:10]([CH:11]([C:12]([OH:14])=[O:13])[OH:17])[OH:21]

Participants

4

Reactant 2

HCID 1045PutrescineHCID 102020809HCID 102020809, compound

Product 1

HCID 13577176HCID 13577176, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

13.225 Grams (150 mmoles) of putrescine (VI) was dissolved in 75 ml of tetrahydrofuran (THF), and a solution of 10.8 g (50 mmoles) of diacetyl-L-tartaric acid anhydride (VIII) in 50 ml of THF was gradually added dropwise thereto while cooling with ice under stirring. After addition, stirring was continued for 2 hours at room temperature, and after completion of the reaction, the solvent was removed by evaporation under reduced pressure. Thereafter, 50 ml of water was added, and the reaction solution was adjusted to pH 13 with 2N NaOH and stirred at room temperature for 2 hours to effect the hydrolysis of the acetyl group.

Workup

  1. temperaturewhile cooling with ice
  2. additionAfter addition
  3. stirringstirring
  4. customafter completion of the reaction
  5. customthe solvent was removed by evaporation under reduced pressure
  6. additionThereafter, 50 ml of water was added
  7. stirringstirred at room temperature for 2 hours
  8. customthe hydrolysis of the acetyl group

Sources & evidence

ORD record
ord-0c84ade155ac4833827288107f784dcc
Source dataset
uspto-grants-1986_07
Patent number
US04603015

Reaction notes

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