Diisopropylethylamine → HCID 59162872, compound

HRID 415879Notes

Reaction equation

HRID 415879 reaction equation
Cl.CO[C:4]([C@@H:6]1[C@H:10]([O:11]C(=O)C2C=CC([N+]([O-])=O)=CC=2)[CH2:9][CH2:8][NH:7]1)=[O:5].[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([OH:31])=O)=[CH:27][C:26]=1[S:34][C:35]([F:38])([F:37])[F:36].CN(C([O:46][N:47]1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>O1CCOCC1.NO>[OH:11][C@@H:10]1[CH2:9][CH2:8][N:7]([C:29](=[O:31])[C:28]2[CH:32]=[CH:33][C:25]([O:24][CH3:23])=[C:26]([S:34][C:35]([F:38])([F:37])[F:36])[CH:27]=2)[C@@H:6]1[C:4]([NH:47][OH:46])=[O:5]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 666198144-Methoxy-3-[(trifluoromethyl)sulfanyl]benzoic acidHCID 66632711HCID 66632711, compound

Product 1

HCID 59162872HCID 59162872, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 787HydroxylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of (2S,3R)-3-(4-nitro-benzoyloxy)-pyrrolidine-2-carboxylic acid methy ester hydrochloride salt prepared by Method C followed by Method F (109 mg, 0.33 mmol), 4-methoxy-3-trifluoromethylsulfanyl-benzoic acid (76.6 mg, 0.30 mmol), in anhydrous dioxane (2.0 mL) was added HATU (136 mg, 0.36 mmol) and DIEA (205 μL, 1.2 mmol) with rapid stirring. The reaction mixture was stirred 2 h at rt then diluted with 50% aq. hydroxylamine (2.0 mL) and stirred an additional 17 h. The crude reaction mixture was purified by preparative reverse phase HPLC to furnish the product (2S,3R)-3-hydroxy-N-hydroxy-1-(4-methoxy-3-trifluoromethylsulfanyl-benzoyl)-pyrrolidine-2-carboxamide (4.0 mg, 4% yield). HPLC: Rt=4.050 min following Method HH; ES−MS: calcd. for C14H15F3N2O5S (380.07). Found: 379.0 [M−H].

Workup

  1. stirringstirred an additional 17 h
  2. customThe crude reaction mixture
  3. customwas purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-2135d3e13a34478594f5bbb4d33727b1
Source dataset
uspto-grants-2012_01
Patent number
US08088804B2

Reaction notes

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