Dimethyl Sulfoxide → HCID 73019240, compound

HRID 1767029Notes

Reaction equation

HRID 1767029 reaction equation
[OH:1][CH2:2][C:3]([C:6]1[S:10][C:9]([NH:11][C:12](=[O:30])[CH:13]([NH:17][CH:18]2[CH2:27][CH2:26][C:25]3[C:20](=[C:21]([F:29])[CH:22]=[C:23]([F:28])[CH:24]=3)[CH2:19]2)[CH2:14][CH2:15][CH3:16])=[N:8][N:7]=1)([CH3:5])[CH3:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CS(C)=O>C(Cl)Cl>[CH3:4][C:3]([C:6]1[S:10][C:9]([NH:11][C:12](=[O:30])[CH:13]([NH:17][CH:18]2[CH2:27][CH2:26][C:25]3[C:20](=[C:21]([F:29])[CH:22]=[C:23]([F:28])[CH:24]=3)[CH2:19]2)[CH2:14][CH2:15][CH3:16])=[N:8][N:7]=1)([CH3:5])[CH:2]=[O:1]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 159087TriacetoxyperiodinaneHCID 729839612-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [5-(2-hydroxy-1,1-dimethyl-ethyl)-[1,3,4]thiadiazol-2-yl]-amide

Product 1

HCID 73019240HCID 73019240, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(6,8-difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [5-(2-hydroxy-1,1-dimethyl-ethyl)-[1,3,4]thiadiazol-2-yl]-amide (60 mg) and Dess-Martin oxidizing agent (100 mg) in methylene chloride (1 mL) and DMSO(1 mL) was stirred at room temperature for 4 hr. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was separated and concentrated. The residue was purified by silica gel column chromatography using 20% to 50% ethyl acetate in hexane as eluent to give 2-(6,8-difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [5-(1,1-dimethyl-2-oxo-ethyl)-[1,3,4]thiadiazol-2-yl]-amide as a brown oil, LC-MS RT=2.1 min, M+1=436.9.0.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4eac11c1a8db4cc5acedc384e5f5185f
Source dataset
uspto-grants-2007_06
Patent number
US07232820B2

Reaction notes

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