Triethylamine → HCID 19106935, compound

HRID 1197604Notes

Reaction equation

HRID 1197604 reaction equation
[C:1]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].O.ON1C2C=CC=CC=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1.Cl.[NH2:47][CH2:48][CH2:49][C:50]1[CH:55]=[CH:54][C:53]([OH:56])=[CH:52][CH:51]=1.C(N(CC)CC)C>C(#N)C.CN(C=O)C>[CH2:4]([O:3][C:1]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([NH:47][CH2:48][CH2:49][C:50]1[CH:55]=[CH:54][C:53]([OH:56])=[CH:52][CH:51]=1)=[O:19])=[O:2])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 66449Tyramine hydrochlorideHCID 747586-(((Phenylmethoxy)carbonyl)amino)hexanoic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 19106935HCID 19106935, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.84 g (3.01 mmol) of N-carbobenzyloxy-ε-aminocaproic acid, 0.39 g (2.89 mmol) of 1-hydroxybenzotriazole hydrate, and 0.59 g (2.86 mmol) of DCC in 3 mL of acetonitrile and 6 mL of DMF is stirred at room temperature under nitrogen for 20 minutes. A quantity of 0.50 g (2.88 mmol) of tyramine hydrochloride followed by 0.40 mL (2.88 mmol) of triethylamine are added and the mixture is stirred for 2 days at room temperature. The mixture is filtered and the filtrate is evaporated. The residue is taken-up into EtOAc, refiltered, and evaporated to give a yellow oil. Purification via silica gel chromatography eluting with 9:1 CHCl3 -MeOH gives crystalline product; wt 0.98 g (88%); mp 107.8°-108.4° C.; MS (CI) 385 (M+1).

Workup

  1. additionare added
  2. stirringthe mixture is stirred for 2 days at room temperature
  3. filtrationThe mixture is filtered
  4. customthe filtrate is evaporated
  5. customevaporated
  6. customto give a yellow oil
  7. customPurification via silica gel chromatography
  8. washeluting with 9:1 CHCl3 -MeOH
  9. customgives crystalline product

Sources & evidence

ORD record
ord-2df59e6843cf449a90874bb82c378b5e
Source dataset
uspto-grants-1994_01
Patent number
US05276048

Reaction notes

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