Triethylamine → HCID 68494934, compound

HRID 446857Notes

Reaction equation

HRID 446857 reaction equation
[Cl:1][C:2]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][S:12]([C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=1)(=[O:14])=[O:13].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH2:61]([O:63][C:64](=[O:67])[CH2:65][NH2:66])[CH3:62]>CN(C)C=O>[CH2:61]([O:63][C:64](=[O:67])[CH2:65][NH:66][C:19](=[O:21])[C:18]1[CH:17]=[CH:16][C:15]([S:12](=[O:13])(=[O:14])[NH:11][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]2[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:2]=2[Cl:1])=[CH:23][CH:22]=1)[CH3:62]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 2723640Glycine ethyl ester, hydrochlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 441384964-[2-(2,4-Dichloro-phenoxy)-phenylsulfamoyl]-benzoic acid

Product 1

HCID 68494934HCID 68494934, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The solution of 4-[2-(2,4-dichloro-phenoxy)-phenylsulfamoyl]-benzoic acid (8.207 g, 18.7 mmol), triethylamine (5.2 mL, 37.4 mmol) and HBTU (8.24 g, 21.7 mmol) in dry dimethyl formamide (150 mL) was stirred at room temperature for five minutes before glycine ethyl ester hydrochloride (Aldrich) (2.614 g, 18.7 mmol) was added. The pH of the reaction mixture was adjusted to 8 by the addition of triethylamine, the so obtained mixture was stirred at room temperature overnight, then concentrated in vacuo. The residue was treated with saturated sodium hydrogencarbonate solution (300 mL), the precipitated crystals were filtered off, washed with water and dried. The crude product was purified by column chromatography using Kieselgel 60 (0.040-0.063 mm) (Merck) as adsorbent, and n-hexane:ethyl acetate=2:1 as eluent to yield 7.68 g (78%) of the title compound. MS (EI) 524 (MH+).

Workup

  1. additionwas added
  2. concentrationconcentrated in vacuo
  3. additionThe residue was treated with saturated sodium hydrogencarbonate solution (300 mL)
  4. filtrationthe precipitated crystals were filtered off
  5. washwashed with water
  6. customdried
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-b78892de75434998b228210878dd65b3
Source dataset
uspto-grants-2013_07
Patent number
US08481527B2

Reaction notes

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