Diisopropylethylamine → HCID 23382096, compound

HRID 1281185Notes

Reaction equation

HRID 1281185 reaction equation
CCN(C(C)C)C(C)C.[CH3:10][O:11][C:12]([NH:14][C@H:15]([C:19]([OH:21])=O)[CH:16]([CH3:18])[CH3:17])=[O:13].[B-](F)(F)(F)F.CN(C(ON1C(=O)C=CC=C1)=[N+](C)C)C.[CH2:42]([N:44]([C:47]1[CH:52]=[CH:51][C:50]([CH2:53][N:54]([NH:67][C:68]([O:70][C:71]([CH3:74])([CH3:73])[CH3:72])=[O:69])[CH2:55][C@H:56]([OH:66])[C@@H:57]([NH2:65])[CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)=[CH:49][CH:48]=1)[CH2:45][CH3:46])[CH3:43]>CN(C=O)C.C(Cl)Cl.CO>[CH2:42]([N:44]([C:47]1[CH:52]=[CH:51][C:50]([CH2:53][N:54]([NH:67][C:68]([O:70][C:71]([CH3:73])([CH3:72])[CH3:74])=[O:69])[CH2:55][C@H:56]([OH:66])[C@@H:57]([NH:65][C:19](=[O:21])[C@H:15]([CH:16]([CH3:17])[CH3:18])[NH:14][C:12]([O:11][CH3:10])=[O:13])[CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)=[CH:49][CH:48]=1)[CH2:45][CH3:46])[CH3:43]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 10647477HCID 10647477, compoundHCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid

Product 1

HCID 23382096HCID 23382096, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

In analogy with Example 2e, 1.5 ml of Hünig's base are added to 0.77 g (4.3 mmol) of N-methoxycarbonyl-(L)-valine and 1.3 g (4.3 mmol) of TPTU in 20 ml of DMF and the whole is stirred at RT for 5 min. After that, 2.0 g (4.3 mmol) of 1-[p-(N,N-diethylamino)phenyl]-4(S)-hydroxy-2-(tert-butyloxycarbonyl)amino-5(S)-amino-6-phenyl-2-azahexane (Example 2d), dissolved in DMF, are added and the mixture is stirred at RT for 2 h. After working up in the same manner as described for Example 2e, the residue is digested in DIPE and the title compound is filtered off. The suction filter residue is washed once again with DIPE and dried in a heated desiccator at 60° C., with the title compound thereby being obtained. TLC: Rf=0.80 (methylene chloride/methanol). HPLC20-100: tret=11.79.

Workup

  1. additionare added
  2. stirringthe mixture is stirred at RT for 2 h
  3. filtrationthe title compound is filtered off
  4. filtrationThe suction filter residue
  5. washis washed once again with DIPE
  6. dry with materialdried in a heated desiccator at 60° C., with the title compound
  7. customthereby being obtained

Sources & evidence

ORD record
ord-d3add5a18b2d46eda252ec26a5fc2d2c
Source dataset
uspto-grants-2002_09
Patent number
US06451973B1

Reaction notes

Loading…