Triethylamine → HCID 131727777, compound

HRID 1436746Notes

Reaction equation

HRID 1436746 reaction equation
[CH3:1][CH:2]([CH3:8])[CH2:3][CH2:4][C:5](O)=[O:6].C(OC([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][C@@H:17]1[C@@H:22]([OH:34])[C@H:23]([NH2:33])[CH2:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[CH:26]=1)=O)(C)(C)C.[ClH:35].CN(C)[CH2:38][CH2:39][CH2:40]N=C=NCC.[OH:47][C:48]1C2N=NNC=2C=[CH:50][CH:49]=1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[ClH:35].[F:31][C:29]1[CH:30]=[C:25]([CH:26]=[C:27]([F:32])[CH:28]=1)[CH2:24][C@H:23]([NH:33][C:48](=[O:47])[CH2:49][CH2:50][CH:39]([CH3:38])[CH3:40])[C@@H:22]([OH:34])[C@H:17]1[CH2:18][N:19]([C:5](=[O:6])[CH2:4][CH2:3][CH:2]([CH3:8])[CH3:1])[CH2:20][CH2:21][NH:16]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 12587Isocaproic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69083684HCID 69083684, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 131727777HCID 131727777, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Combine 4-methyl-pentanoic acid (0.047 mL, 0.37 mmol), 2-(R)-[(2-(R)-amino-1-(S)-hydroxy-3-(3,5-difluoro-phenyl)propyl)]piperzine-1-carboxylic acid tert-butyl ester (63 mg, 0.17 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (78 mg, 0.41 mmol), hydroxybenzotriazole (50 mg, 0.41 mmol), triethylamine (0.095 mL, 0.68 mmol), and 4-dimethylaminopyridine (4.6 mg, 0.04 mmol) in 2 mL dichloromethane. Stir at room temperature over night. Subject reaction mixture to silica gel chromatography, eluting with 97:3 dichloromethane:methanol. Stir residue in 4M HCl in 1,4-dioxane over night. Concentrate under reduced pressure to provide the title compound (39 mg, 49%) as a white solid.

Workup

  1. customreaction mixture to silica gel chromatography
  2. washeluting with 97:3 dichloromethane
  3. waitStir residue in 4M HCl in 1,4-dioxane over night
  4. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-a94c9d076e0b4825939024029d9f7346
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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