Diisopropylethylamine → HCID 53993942, compound

HRID 2287898Notes

Reaction equation

HRID 2287898 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]([C@H:20]([CH2:24][C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=3)[C:21](O)=[O:22])[CH3:19])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.ON1C2N=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[C:57]([O:61][C:62]([N:64]([CH3:78])[NH:65][C:66](=[O:77])[C@H:67]([NH:75][CH3:76])[CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)=[O:63])([CH3:60])([CH3:59])[CH3:58].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:57]([O:61][C:62]([N:64]([CH3:78])[NH:65][C:66](=[O:77])[C@H:67]([N:75]([C:21](=[O:22])[C@H:20]([N:18]([C:16]([O:15][CH2:14][CH:12]1[C:13]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:17])[CH3:19])[CH2:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1)[CH3:76])[CH2:68][C:69]1[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=1)=[O:63])([CH3:58])([CH3:60])[CH3:59]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 54171762HCID 54171762, compoundHCID 54260881HCID 54260881, compound

Product 1

HCID 53993942HCID 53993942, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (2R)-2-[N-(9H-fluoren-9-ylmethoxycarbonyl)-N-methylamino]-3-naphthalen-2-ylpropionic acid (0.6 g, 1.33 mmol) in methylene chloride (10 ml) was added 1-hydroxy-7-azabenzotriazole (0.18 g, 1.33 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.25 g, 1.33 mmol) and the mixture was cooled to 0° C. Then N-methyl-N'-((2R)-2-(methylamino)-3-phenylpropionyl)hydrazinecarboxylic acid tert-butyl ester (0.34 g, 1.11 mmol) and diisopropylethylamine (0.25 ml, 1.44 mmol) were added and the mixture was stirred at room temperature overnight. Then methylene chloride (50 ml) was added and the mixture was washed with water (10 ml), saturated sodium bicarbonate (10 ml), brine (10 ml), dried (MgSO4), filtered and concentrated in vacuo. The product was chromatographed on silica (40 g) with heptane:ethyl acetate (2:1) to give 0.53 g (64%) of N'-[(2R)-2-(N-((2R)-2-[N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-methylamino]-3-(2-naphthyl)propionyl)-N-methylamino)-3-phenylpropionyl]-N-methylhydrazinecarboxylic acid tert-butyl ester as a colourless oil.

Workup

  1. washthe mixture was washed with water (10 ml), saturated sodium bicarbonate (10 ml), brine (10 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was chromatographed on silica (40 g) with heptane:ethyl acetate (2:1)

Sources & evidence

ORD record
ord-559eb664bf314622896686bddb61bcc7
Source dataset
uspto-grants-2000_07
Patent number
US06083908

Reaction notes

Loading…