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Hydrochloric Acid → HCID 19424596, compound

HRID 743500
Notes
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Reaction equation

HRID 743500 reaction equation
[CH2:1]1[N:8]([CH2:9][CH2:10][NH+:11]([CH2:22][C:23]([O-:25])=[O:24])[CH2:12][CH2:13][N:14]2[CH2:21][C:19](=[O:20])[O:18][C:16](=[O:17])[CH2:15]2)[CH2:7][C:5](=[O:6])[O:4][C:2]1=[O:3].[NH2:26][CH2:27][CH2:28][CH2:29][CH2:30][NH2:31].Cl>CN(C=O)C.CN(C=O)C.C1CN2C(=NCCC2)C1>[C:16]([CH2:15][N:14]1[CH2:21][C:19](=[O:20])[NH:31][CH2:30][CH2:29][CH2:28][CH2:27][NH:26][C:2](=[O:3])[CH2:1][N:8]([CH2:7][C:5]([OH:6])=[O:4])[CH2:9][CH2:10][N:11]([CH2:22][C:23]([OH:25])=[O:24])[CH2:12][CH2:13]1)([OH:18])=[O:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1045PutrescineHCID 16760401Diethylenetriaminepentaacetic dianhydride

Product 1

HCID 19424596HCID 19424596, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×
HCID 131719551
HCID 131719551, compound
Solvent

Procedure

A 1 L three-neck flask was charged with 340 mL of dry DMF. Two syringes were charged separately with solutions of diethylenetriaminepentaacetic acid dianhydride (3.00 g, 8.40 mmol) in 100 mL of DMF and 1,4-diaminobutane (0.740 g, 8.40 mmol) in DMF/DBN, (96 mL/4 mL). The solutions were added simultaneously at ambient temperature to the flask at a rate of 30 mL/hour. After the addition was complete, the reaction mixture was allowed to stir overnight, stripped to dryness, and 1N HCl added to adjust the pH to 10.4. The solution was applied to AG1-X8 (100-200 mesh, OAc-) resin and eluted with 0.5N acetic acid to yield 0.52 g (13.6%) as a white solid, after removal of acetic acid and lyophilization.

Workup

  1. additionThe solutions were added simultaneously at ambient temperature to the flask at a rate of 30 mL/hour
  2. additionAfter the addition
  3. additionadded
  4. washeluted with 0.5N acetic acid
  5. customto yield 0.52 g (13.6%) as a white solid
  6. customafter removal of acetic acid and lyophilization

Sources & evidence

ORD record
ord-1dcdd200f8024a8398612ef6a82c7878
Source dataset
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05556968

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes