Tris(2-aminoethyl)amine → HCID 53641123, compound

HRID 2287901Notes

Reaction equation

HRID 2287901 reaction equation
C1C2C(CO[C:16](=O)[N:17]([C@@H:19]([C:31](=[O:50])[N:32]([C@H:34]([CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:35]([NH:37][N:38]([C:40](=[O:42])[CH3:41])[CH3:39])=[O:36])[CH3:33])[CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=3)C)C3C(=CC=CC=3)C=2C=CC=1.NCCN(CCN)CCN>C(Cl)Cl>[C:40]([N:38]([CH3:39])[NH:37][C:35](=[O:36])[C@H:34]([N:32]([CH3:33])[C:31](=[O:50])[C@H:19]([NH:17][CH3:16])[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1)[CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)(=[O:42])[CH3:41]

Participants

4

Reactant 2

HCID 77731Tris(2-aminoethyl)amineHCID 53729521HCID 53729521, compound

Product 1

HCID 53641123HCID 53641123, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-((1R)-1-(N-[(1R)-2-(N'-acetyl-N'-methylhydrazino)-1-benzyl-2-oxoethyl]-N-methylcarbamoyl)-2-(2-naphthyl)ethyl)-N-methylcarbamic acid ((9H-fluoren-9-yl)methyl) ester (0.21 g, 0.31 mmol) in methylene chloride (4 ml) was added tris(2-aminoethyl)amine (4 ml) and the mixture was stirred for 60 min. Then methylene chloride (50 ml) was added and the mixture was washed with brine (2×20 ml), phosphate buffer (pH=6, 2×20 ml), water (20 ml), brine (10 ml), dried (MgSO4), filtered and concentrated in vacuo to give 0.13 g (92%) of (2R)-N-[(1R)-2-(N'-acetyl-N'-methylhydrazino)-1-benzyl-2-oxoethyl]-N-methyl-2-(methylamino)-3-(2-naphthyl)propionamide as a colourless oil.

Workup

  1. washthe mixture was washed with brine (2×20 ml), phosphate buffer (pH=6, 2×20 ml), water (20 ml), brine (10 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09566b39d037491c9af5e18ec20b9631
Source dataset
uspto-grants-2000_07
Patent number
US06083908

Reaction notes

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