Triethylamine → HCID 178465179, compound

HRID 907445Notes

Reaction equation

HRID 907445 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:25]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[C@H:26]([C:48]([OH:50])=O)[CH2:27][CH2:28][CH2:29][NH:30][C:31](=[NH:47])[NH:32][S:33]([C:36]1[C:45]([CH3:46])=[C:43]([CH3:44])[C:40]([O:41][CH3:42])=[CH:39][C:37]=1[CH3:38])(=[O:35])=[O:34].[NH:58]1[CH2:67][CH2:66][CH2:65][C@H:59]1[C:60]([NH:62][CH2:63][CH3:64])=[O:61].Cl.C(N(CC)CC)C>CC(N(C)C)=O>[NH:25]([C:51]([O:53][C:54]([CH3:56])([CH3:57])[CH3:55])=[O:52])[C@H:26]([C:48]([N:58]1[CH2:67][CH2:66][CH2:65][C@H:59]1[C:60]([NH:62][CH2:63][CH3:64])=[O:61])=[O:50])[CH2:27][CH2:28][CH2:29][NH:30][C:31](=[NH:47])[NH:32][S:33]([C:36]1[C:45]([CH3:46])=[C:43]([CH3:44])[C:40]([O:41][CH3:42])=[CH:39][C:37]=1[CH3:38])(=[O:34])=[O:35]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 22804123N-Ethyl-L-prolinamide--hydrogen chloride (1/1)HCID 178491780HCID 178491780, compound

Product 1

HCID 178465179HCID 178465179, compoundYield 131.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent4×

Procedure

According to the general procedure for HBTU promoted coupling solutions of 31.5 g Boc-Arg(Mtr)-OH in DMAC, 24.79 g HBTU in DMAC, 11.56 g H-Pro-NHEt.HCl in DMAC and 19.60 g triethylamine in DMAC were premixed and fed into the reactor at 50° C. using a residence time of 1.1 min to yield 52 g crude material which was used in the next step without purification. The calculated yield from HPLC analysis was 99%.

Workup

  1. customfed into the reactor at 50° C.
  2. customa residence time of 1.1 min

Sources & evidence

ORD record
ord-4761f4b5141b44c696910bb0443a7032
Source dataset
uspto-grants-2011_09
Patent number
US08013117B2

Reaction notes

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