Diisopropylethylamine → HCID 11082969, compound

HRID 1281184Notes

Reaction equation

HRID 1281184 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.Cl.[CH2:43]([N:45]([C:48]1[CH:53]=[CH:52][C:51]([CH2:54][N:55]([NH2:80])[CH2:56][C@H:57]([OH:79])[C@@H:58]([NH:66][C:67](=[O:78])[C@H:68]([C:74]([CH3:77])([CH3:76])[CH3:75])[NH:69][C:70]([O:72][CH3:73])=[O:71])[CH2:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)=[CH:50][CH:49]=1)[CH2:46][CH3:47])[CH3:44]>CN(C=O)C>[CH2:43]([N:45]([C:48]1[CH:53]=[CH:52][C:51]([CH2:54][N:55]([NH:80][C:19](=[O:21])[C@H:15]([CH:16]([CH3:17])[CH3:18])[NH:14][C:12]([O:11][CH3:10])=[O:13])[CH2:56][C@H:57]([OH:79])[C@@H:58]([NH:66][C:67](=[O:78])[C@H:68]([C:74]([CH3:76])([CH3:75])[CH3:77])[NH:69][C:70]([O:72][CH3:73])=[O:71])[CH2:59][C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=2)=[CH:50][CH:49]=1)[CH2:46][CH3:47])[CH3:44]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidHCID 23382091HCID 23382091, compound

Product 1

HCID 11082969HCID 11082969, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In analogy with Example 2, 0.42 ml of Hünig's base is added to 0.193 g (1.1 mmol) of N-methoxycarbonyl-(L)-valine and 0.327 g (1.1 mmol) of TPTU in 3 ml of DMF and the whole is stirred at RT for 10 min. After that, 0.63 g (1 mmol) of 1-[p-(N,N-diethylamino)-phenyl]-4(S)-hydroxy-2-amino-5(S)-[N-(N-methoxycarbonyl-(L)-tert-leucyl)amino]-6-phenyl-2-azahexane hydrochloride (Example 2f), dissolved in 2 ml of DMF, is added and the mixture is stirred at RT for 21 h. After working-up in the same way as described for Example 2, 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 45° C. TLC: Rf0.50 (ethyl acetate). HPLC20-100: tret=10.93; FAB MS (M+H)+=685.

Workup

  1. additionis added
  2. stirringthe mixture is stirred at RT for 21 h
  3. filtrationthe title compound is filtered off
  4. filtrationThe suction filter residue
  5. washis washed once again with DIPE
  6. customdried in a heated desiccator at 45° C

Sources & evidence

ORD record
ord-f90c7e762bdb4dcbba289b8d9aba3394
Source dataset
uspto-grants-2002_09
Patent number
US06451973B1

Reaction notes

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