Triethylamine → HCID 22176544, compound

HRID 1797198Notes

Reaction equation

HRID 1797198 reaction equation
C(Cl)(=O)C(Cl)=O.Cl.[CH3:8][N:9]([CH3:16])[CH2:10][CH2:11][CH2:12][C:13](O)=[O:14].[OH:17][C:18]([C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-])=O)=[CH:30][CH:29]=1)([CH3:27])[CH2:19][NH:20][S:21]([CH:24]([CH3:26])[CH3:25])(=[O:23])=[O:22].C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C.C1COCC1>[CH3:8][N:9]([CH3:16])[CH2:10][CH2:11][CH2:12][C:13]([NH:34][C:31]1[CH:30]=[CH:29][C:28]([C:18]([OH:17])([CH3:27])[CH2:19][NH:20][S:21]([CH:24]([CH3:25])[CH3:26])(=[O:23])=[O:22])=[CH:33][CH:32]=1)=[O:14]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 126916404-(Dimethylamino)butyric acid hydrochlorideHCID 22176567HCID 22176567, compound

Product 1

HCID 22176544HCID 22176544, compoundYield 59.7%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into a 50 mL single-neck flask, 1 mL of oxalyl chloride was added syringe wise to 306 mg of 4-(dimethylamino)butyric acid hydrochloride in CH2Cl2 (20 mL) while stirring under a nitrogen atmosphere at room temperature. Then at this temperature. 1 drop of DMF was added by pipette and the mixture began to foam. The reaction was allowed to stir at this temperature for 1 h and was then concentrated under reduced vacuum to yield a yellow solid. This solid was added portion wise to a 100 mL single-neck flask containing 460 mg of [2-(4-aminophenyl)-2-hydroxypropyl][(methylethyl)sulfonyl]amine (prepared in example 19) and 183 mg of triethylamine in THF (25 mL) while stirring at room temperature under a nitrogen atmosphere. After 2 h at this temperature, the mixture was concentrated under reduced vacuum and the resulting solid was taken into ethyl acetate. The organic layer was backwashed once with H2O, dried over K2CO3, and concentrated under reduced vacuum to yield 794 mg as an oil. This material was purified via silica gel chromatography employing the Chromatotron while using a 4000 micron rotor and eluting with an isocratic solvent of methanol/1% NH4OH to yield intermediate title compound (350 mg, 51%) as a viscous oil. Ion spray M.S. 385 (M*).

Workup

  1. stirringto stir at this temperature for 1 h
  2. concentrationwas then concentrated under reduced vacuum
  3. customto yield a yellow solid
  4. additionThis solid was added portion wise to a 100 mL single-neck flask
  5. stirringwhile stirring at room temperature under a nitrogen atmosphere
  6. concentrationthe mixture was concentrated under reduced vacuum
  7. dry with materialdried over K2CO3
  8. concentrationconcentrated under reduced vacuum
  9. customto yield 794 mg as an oil
  10. customThis material was purified via silica gel chromatography
  11. washeluting with an isocratic solvent of methanol/1% NH4OH

Sources & evidence

ORD record
ord-987008a144284dabb1d1e2ab7aef2d20
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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