1,2-Dichloroethane → HCID 23382086, compound

HRID 1281191Notes

Reaction equation

HRID 1281191 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:10]([OH:12])=O)[CH:7]([CH3:9])[CH3:8])=[O:4].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[CH3:34][N:35]1[CH2:40][CH2:39][N:38]([C:41]2[CH:46]=[CH:45][C:44]([CH2:47][N:48]([NH:61][C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[CH2:49][C@H:50]([OH:60])[C@@H:51]([NH2:59])[CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)=[CH:43][CH:42]=2)[CH2:37][CH2:36]1>CN(C=O)C>[CH3:34][N:35]1[CH2:36][CH2:37][N:38]([C:41]2[CH:46]=[CH:45][C:44]([CH2:47][N:48]([NH:61][C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[CH2:49][C@H:50]([OH:60])[C@@H:51]([NH:59][C:10](=[O:12])[C@H:6]([CH:7]([CH3:8])[CH3:9])[NH:5][C:3]([O:2][CH3:1])=[O:4])[CH2:52][C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)=[CH:43][CH:42]=2)[CH2:39][CH2:40]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidHCID 23382085HCID 23382085, compound

Product 1

HCID 23382086HCID 23382086, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.60 g (9.16 mmol) of N-methoxycarbonyl-(L)-valine, 3.29 g (17.16 mmol) of EDC and 1.54 g (11.4 mmol) of HOBT are dissolved, under a N2 atmosphere, in 49 ml of DMF. After 20 min at RT, 4.8 ml (34.4 mmol) of triethylamine are added. 2.77 g (5.7 mmol) of 1-[p-(4-methylpiperazin-1-yl)phenyl]-4(S)-hydroxy-2-(tert-butyloxycarbonyl)amino-5(S)-amino-6-phenyl-2-azahexane in 24 ml of DMF are then added and the whole is thoroughly stirred overnight. The reaction mixture is evaporated under HV and the residue is dissolved in methylene chloride and a little methanol; this solution is then washed with sat. NaHCO3 solution, water and brine. The aqueous phases are extracted twice with methylene chloride. The combined organic phases are dried (Na2SO4) and concentrated by evaporation. Precipitating with DIPE from a concentrated solution in boiling methylene chloride results in the title compound:

Workup

  1. waitthe whole is thoroughly stirred overnight
  2. customThe reaction mixture is evaporated under HV
  3. dissolutionthe residue is dissolved in methylene chloride
  4. washthis solution is then washed with sat. NaHCO3 solution, water and brine
  5. extractionThe aqueous phases are extracted twice with methylene chloride
  6. dry with materialThe combined organic phases are dried (Na2SO4)
  7. concentrationconcentrated by evaporation
  8. customPrecipitating with DIPE from a concentrated solution

Sources & evidence

ORD record
ord-530061ee460443a282603a021733ee98
Source dataset
uspto-grants-2002_09
Patent number
US06451973B1

Reaction notes

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