Pyridine → HCID 178512915, compound

HRID 1482158Notes

Reaction equation

HRID 1482158 reaction equation
CCN(C(C)C)C(C)C.[NH2:10][C@H:11]([C:22]([N:24]1[CH2:31][CH2:30][CH2:29][C@H:25]1[C:26]([OH:28])=[O:27])=[O:23])[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1.[NH:32]([C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[C@H:33]([C:41](O)=[O:42])[CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:40])[NH2:39].Cl.N1C=CC=CC=1.C(Cl)(=O)C(C)(C)C>CC(N(C)C)=O>[NH:32]([C:44]([O:46][CH2:47][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)=[O:45])[C@H:33]([C:41]([NH:10][C@H:11]([C:22]([N:24]1[CH2:31][CH2:30][CH2:29][C@H:25]1[C:26]([OH:28])=[O:27])=[O:23])[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)=[O:42])[CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:39])[NH2:40]

Participants

7

Reactant 5

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 81531Diisopropylethylamine2×HCID 9839333L-Tryptophyl-L-prolineHCID 178479461HCID 178479461, compound

Product 1

HCID 178512915HCID 178512915, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

DMA, 1.00 equivalent of DIPEA and 1.00 equivalent of H-Trp-Pro-OH (Mw=301.3; purity=94.0%) were mixed at room temperature for at least 30 min until a solution was obtained and then the solution was cooled to 10±5° (solution No. 1). 1.00 equivalent of Z-Arg-OH.HCl (Mw=344.8) were added to DMA at room temperature until a clear solution was obtained (solution No. 2). While cooling solution No. 2 to −15±5° C., 1.05 equivalents pyridine (Mw=79.1; purity=99.0%) and 1.00 equivalent of DIPEA were added. Once this temperature was reached, 1.00 equivalent of pivaloyl chloride (PivCl) (Mw=120.58) was poured into the reaction mixture (solution No. 2) which was further activated for about 5 minutes. Finally, solution No. 1 was added to the activated solution No. 2 and the reaction mixture was further stirred for at least 1 hour while cooling was stopped and the reaction mixture allowed to warm up to room temperature.

Workup

  1. customwas obtained
  2. temperaturethe solution was cooled to 10±5° (solution No. 1)
  3. customwas obtained (solution No
  4. temperatureWhile cooling solution No
  5. addition1 was added to the activated solution No
  6. temperaturewhile cooling

Sources & evidence

ORD record
ord-5542ae4ae4094790bef2cb2a78516733
Source dataset
uspto-grants-2016_08
Patent number
US09409946B2

Reaction notes

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