Triethylamine → HCID 68590963, compound

HRID 736954Notes

Reaction equation

HRID 736954 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[CH3:30][N:31]1[CH2:36][CH2:35][N:34]([CH:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[CH2:33][CH2:32]1.[NH2:43][C:44]1[C:49]([C:50]([F:53])([F:52])[F:51])=[CH:48][C:47]([CH2:54][C@@H:55]([O:59][CH2:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[C:56](O)=[O:57])=[CH:46][C:45]=1[Cl:67]>C1COCC1>[NH2:43][C:44]1[C:49]([C:50]([F:51])([F:52])[F:53])=[CH:48][C:47]([CH2:54][C@@H:55]([O:59][CH2:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[C:56]([N:40]2[CH2:41][CH2:42][CH:37]([N:34]3[CH2:35][CH2:36][N:31]([CH3:30])[CH2:32][CH2:33]3)[CH2:38][CH2:39]2)=[O:57])=[CH:46][C:45]=1[Cl:67]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 7957071-Methyl-4-(piperidin-4-yl)piperazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68593018HCID 68593018, compound

Product 1

HCID 68590963HCID 68590963, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.35 g (4.20 mmol) TBTU, 0.70 mL (5.0 mmol) triethylamine and 0.75 g (4.01 mmol) 1-methyl-4-piperidin-4-yl-piperazine were added to a solution of 1.5 g (4.01 mmol) (R)-3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-benzyloxy-propionic acid in 50 mL THF and the reaction mixture was stirred overnight at RT. The reaction solution was evaporated down i.vac., the residue was combined with 200 mL EtOAc and 200 mL saturated NaHCO3 solution, the organic phase was separated off and extracted with 100 mL of 5% citric acid solution. The citric acid extract was made alkaline with K2CO3 and extracted twice with 100 mL EtOAc in each case. The combined organic phases were evaporated down i.vac. and the residue further reacted without purification.

Workup

  1. customThe reaction solution was evaporated down i.vac
  2. customthe organic phase was separated off
  3. extractionextracted with 100 mL of 5% citric acid solution
  4. extractionThe citric acid extract
  5. extractionextracted twice with 100 mL EtOAc in each case
  6. customThe combined organic phases were evaporated down i.vac
  7. customand the residue further reacted without purification

Sources & evidence

ORD record
ord-64d7df4128d74494a20ec7b93db2906f
Source dataset
uspto-grants-2009_09
Patent number
US07595312B2

Reaction notes

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