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Oxalyl chloride → N-(3-tert-butyl-isoxazol-5-ylmethyl)-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionamide

HRID 628776
Notes
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Reaction equation

HRID 628776 reaction equation
[CH3:1][C:2]([S:7]([CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)(=[O:9])=[O:8])([CH3:6])[C:3]([OH:5])=O.C(Cl)(=O)C(Cl)=O.[C:22]([C:26]1[CH:30]=[C:29]([CH2:31][NH2:32])[O:28][N:27]=1)([CH3:25])([CH3:24])[CH3:23].C(N(CC)C(C)C)(C)C>CN(C=O)C.C(Cl)Cl>[C:22]([C:26]1[CH:30]=[C:29]([CH2:31][NH:32][C:3](=[O:5])[C:2]([CH3:1])([S:7]([CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)(=[O:9])=[O:8])[CH3:6])[O:28][N:27]=1)([CH3:25])([CH3:23])[CH3:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 597040272-Methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionic acidHCID 64157435(3-Tert-butyl-1,2-oxazol-5-yl)methanamine

Product 1

HCID 67325131N-(3-tert-butyl-isoxazol-5-ylmethyl)-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionamideYield 44%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Activation of 51 mg (0.22 mmol) of 2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionic acid as the corresponding acid chloride is achieved by treatment with oxalyl chloride (0.04 mL) and DMF (1 drop) in DCM (2 mL) at room temperature for 1 h. The reaction is concentrated under reduced pressure. The crude acid chloride is dissolved in DCM (1 mL) and added dropwise to a solution of (3-tert-butyl-1,2-oxazol-5-yl)methanamine (42 mg, 80%, 0.22 mmol) and N,N-diisopropylethylamine (114 μL, 0.66 mmol) in DCM (2 mL). The reaction is concentrated under reduced pressure. The residue is purified twice by column chromatography (silica, eluent: heptanes, 0-50% ethyl acetate then DCM, 20% ethyl acetate), followed by preparative HPLC (neutral method) to give 36 mg of N-(3-tert-butyl-isoxazol-5-ylmethyl)-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-propionamide. Yield: 44%; ES-MS: m/z 373 [M+H]. Compounds in Table 4 amide method D are made according to this procedure.

Workup

  1. concentrationThe reaction is concentrated under reduced pressure
  2. dissolutionThe crude acid chloride is dissolved in DCM (1 mL)
  3. concentrationThe reaction is concentrated under reduced pressure
  4. customThe residue is purified twice by column chromatography (silica, eluent

Sources & evidence

ORD record
ord-444e031952944cbea500f1087f426aeb
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09315454B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes