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Triethylamine → HCID 18365431, compound

HRID 380589
Notes
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Reaction equation

HRID 380589 reaction equation
[CH3:1][C:2]([NH:7][S:8]([C:11]1[S:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:14][CH:15]=1)(=[O:10])=[O:9])([CH3:6])[C:3]([OH:5])=O.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.[CH3:57][Si:58]([CH3:64])([CH3:63])[CH2:59][CH2:60][O:61][NH2:62]>C(Cl)Cl>[CH3:6][C:2]([NH:7][S:8]([C:11]1[S:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:14][CH:15]=1)(=[O:10])=[O:9])([CH3:1])[C:3]([NH:62][O:61][CH2:60][CH2:59][Si:58]([CH3:64])([CH3:63])[CH3:57])=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 18365440HCID 18365440, compoundHCID 18419632O-(2-(Trimethylsilyl)ethyl)hydroxylamine--hydrogen chloride (1/1)

Product 1

HCID 18365431HCID 18365431, compoundYield 10.1%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-2-(5-pyridin-2-ylthiophene-2-sulfonylamino)-propionic acid (1.60 grams, 4.91 mmole) in methylene chloride (160 mL) was added triethylamine (2.3 mL, 16.5 mmole), (benzotriazol-1-yloxy)tris(dimethylamino)-phosphonium hexafluorophosphate (2.4 grams, 5.41 mmole) and O-(2-trimethylsilylethyl)hydroxylamine hydrochloride (0.92 grams, 5.41 mmole). The resulting mixture was stirred at room temperature for 16 hours. The solvent was evaporated and the residue was taken up in ethyl acetate. The solution was washed with water, aqueous saturated sodium bicarbonate solution, and brine. After drying over magnesium sulfate, the solvent was evaporated to afford a white foam from which the desired product, 2-methyl-2-(5-pyridin-2-ylthiophene-2-sulfonylamino)-N-(2-trimethylsilanylethoxy)-propionamide (220 mg, 10%), a white solid, was isolated by chromatography on silica gel eluting with 3:2 ethyl acetate/hexanes.

Workup

  1. customThe solvent was evaporated
  2. washThe solution was washed with water, aqueous saturated sodium bicarbonate solution, and brine
  3. dry with materialAfter drying over magnesium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2589f8a081ee4ed38e5a974def48aa72
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06303636B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes