Dimethylformamide → HCID 131720985, compound

HRID 380237Notes

Reaction equation

HRID 380237 reaction equation
Cl.Cl.Cl.[N:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]([NH2:42])[CH2:18][C@H:19]([OH:41])[C@@H:20]([NH:28][C:29](=[O:40])[C@H:30]([C@H:36]([CH2:38][CH3:39])[CH3:37])[NH:31][C:32]([O:34][CH3:35])=[O:33])[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:12][CH:11]=1.COC([NH:47][C@H:48]([C:52]([OH:54])=O)[CH:49]([CH3:51])[CH3:50])=O.[B-](F)(F)(F)F.CN([C:63]([O:67]N1C(=O)C=CC=C1)=[N+](C)C)C.C1CCN2C(=NCCC2)CC1.CN([CH:89]=[O:90])C>>[N:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:11]=[CH:12][C:13]([CH2:16][N:17]([NH:42][C:52](=[O:54])[C@H:48]([CH:49]([CH3:50])[CH:51]=[C:63]=[O:67])[NH:47][O:90][CH3:89])[CH2:18][C@H:19]([OH:41])[C@@H:20]([NH:28][C:29](=[O:40])[C@H:30]([C@H:36]([CH2:38][CH3:39])[CH3:37])[NH:31][C:32]([O:34][CH3:35])=[O:33])[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 5

HCID 6228Dimethylformamide2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidHCID 66577958HCID 66577958, compound

Product 1

HCID 131720985HCID 131720985, compound

Procedure

Analogously to Example 46, 0.96 g (1.5 mmol) of 1-[4-(pyridin-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-iso-leucyl)amino-6-phenyl-2-azahexane 3HCl (Example 47d) in 10 ml of DMF are reacted with 0.263 g (1.5 mmol) of N-methoxycarbonyl-(L)-valine, 0.446 g (1.5 mmol) of TPTU and 0.78 ml (4.5 mmol) of DBU in 7 ml of DMF. After working up, the title compound is obtained: TLC: Rf=0.4 (ethyl acetate); HPLC20-100: tRet=11.23. FAB MS (M+H)+=691.

Sources & evidence

ORD record
ord-2c639d3b989d4981847829e087d2bb1f
Source dataset
uspto-grants-2001_10
Patent number
US06300519B1

Reaction notes

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