Triethylamine → HCID 71133773, compound

HRID 1523113Notes

Reaction equation

HRID 1523113 reaction equation
[C:1]([CH2:8][N:9]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16][N:15]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[N+:36]([C:39]1[CH:46]=[CH:45][C:42]([CH2:43]Br)=[CH:41][CH:40]=1)([O-:38])=[O:37]>C(Cl)(Cl)Cl>[C:22]([CH2:21][N:15]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10][N:9]([CH2:8][C:1]([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2])[CH2:20][CH2:19][N:18]([CH2:43][C:42]2[CH:45]=[CH:46][C:39]([N+:36]([O-:38])=[O:37])=[CH:40][CH:41]=2)[CH2:17][CH2:16]1)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 660114-Nitrobenzyl bromideHCID 3938811,7-Bis(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane

Product 1

HCID 71133773HCID 71133773, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of compound (20) (1.85 g, 4.62 mmol) in dry CHCl3 (50 ml) were added triethylamine (1.93 ml, 1.40 g, 13.86 mmol) and 4-nitrobenzylbromide (0.99 g, 4.62 mmol). After stirring the mixture at an ambient temperature for 10 hours, the solvent was removed under reduced pressure, and the residue was purified via alumina (basic) column chromatography. Extraction with ethyl acetate/methanol (10:2) gave a solidified clear oily compound (21) (1.98 g, 80% yield).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue was purified via alumina (basic) column chromatography
  3. extractionExtraction with ethyl acetate/methanol (10:2)

Sources & evidence

ORD record
ord-06bec51a296a4232bff1996ff1e05338
Source dataset
uspto-grants-2015_07
Patent number
US09079867B2

Reaction notes

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