Benzylamine → N-benzyl-2-(tert-butoxycarbonylamino)-5-indan carboxamide

HRID 48431Notes

Reaction equation

HRID 48431 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]([OH:20])=O)[CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C>C(Cl)Cl>[CH2:21]([NH:28][C:18]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:17]2)=[O:20])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 227195982-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-indene-5-carboxylic acid

Product 1

HCID 22719645N-benzyl-2-(tert-butoxycarbonylamino)-5-indan carboxamideYield 86.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using 2-(tert-butoxycarbonylamino)-5-carboxyindan (400 mg, 1.44 mmol), benzylamine (0.24 ml, 2.2 mmol), triethylamine (1.4 ml, 10 mmol), propanephosphonic acid anhydride (2.1 ml), dimethylaminopyridine (a catalytic amount) and methylene chloride (12 ml), a similar procedure to a) in Production Example 218 was carried out. The product obtained was purified by silica gel chromatography (methylene chloride:methanol=95:5) to obtain N-benzyl-2-(tert-butoxycarbonylamino)-5-indan carboxamide (460 mg, 1.25 mmol) having the following physical properties:

Workup

  1. customThe product obtained
  2. customwas purified by silica gel chromatography (methylene chloride:methanol=95:5)

Sources & evidence

ORD record
ord-37867869003c4ee1a138abb8fa60fffa
Source dataset
uspto-grants-2004_03
Patent number
US06703421B1

Reaction notes

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