Triethylamine → HCID 178512830, compound

HRID 261330

Reaction equation

HRID 261330 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:16][SH:17])[C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7].[N+]([O-])(O)=O.[C:22](C1C(C)=NNC=1C)(=[NH:24])[NH2:23].C(N(CC)CC)C>CN(C)C=O>[NH:1]([CH2:2][CH2:3][CH2:4][CH:5]([CH2:16][SH:17])[C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])[C:22]([NH2:24])=[NH:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 127697271-(5-Amino-2-mercaptomethylpentanoyl)-L-prolineHCID 136347471Guanyl-3,5-dimethylpyrazole nitrate

Product 1

HCID 178512830HCID 178512830, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(5-amino-2-mercaptomethylpentanoyl)-L-proline (2.3 g), guanyl-3,5-dimethylpyrazole nitrate (2.41 g) and triethylamine (3.36 ml) in dimethylformamide (20 ml) is stored at room temperature under a blanket of argon for sixteen hours. The solvents are removed in vacuo, the residue is dissolved in 0.1 N hydrochloric acid (10 ml) and zinc dust (500 mg) is added. The suspension is stirred at room temperature for two hours. After filtering, the filtrate is applied to a column of Dowex 50 ion exchange resin in the hydrogen cycle. The column is washed with water until no more acid is eluted and 1-(5-guanidino-2-mercaptomethylpentanoyl)-L-proline is then eluted with a pyridine-acetate buffer at pH 6.5.

Workup

  1. customThe solvents are removed in vacuo
  2. dissolutionthe residue is dissolved in 0.1 N hydrochloric acid (10 ml)
  3. additionzinc dust (500 mg) is added
  4. filtrationAfter filtering
  5. washThe column is washed with water until no more acid
  6. washis eluted
  7. wash1-(5-guanidino-2-mercaptomethylpentanoyl)-L-proline is then eluted with a pyridine-acetate buffer at pH 6.5

Sources & evidence

ORD record
ord-b777e3c9eaa349a1a26483767b03ec92
Source dataset
uspto-grants-1979_08
Patent number
US04165320

Linked notes

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