Methanol → HCID 178517934, compound

HRID 46130Notes

Reaction equation

HRID 46130 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[NH:8][C:9]1[S:10][C:11]([CH2:22][CH2:23]OS(C)(=O)=O)([CH2:15][CH2:16]OS(C)(=O)=O)[C:12](=[O:14])[N:13]=1.[CH:29]1([NH2:34])[CH2:33][CH2:32][CH2:31][CH2:30]1.CO>C(Cl)Cl>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[NH:8][C:9]1[S:10][C:11]2([CH2:22][CH2:23][N:34]([CH:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)[CH2:16][CH2:15]2)[C:12](=[O:14])[N:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 2906CyclopentylamineHCID 178505285HCID 178505285, compound

Product 1

HCID 178517934HCID 178517934, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of methanesulfonic acid 2-[2-(bicyclo[2.2.1]hept-2-ylamino)-5-(2-methanesulfonyloxy-ethyl)-4-oxo-4,5-dihydro-thiazol-5-yl]-ethyl ester (half of the crude product from above) and cyclopentylamine (799 mg, 9.38 mmol) in CH2Cl2 (1.5 mL) was stirred at room temperature for 4 d. Flash column chromatography (silica gel, 0-10% MeOH in CH2Cl2) afforded the title compound as an off-white solid (52 mg). MS (ESI, pos. ion) m/z: 348 (M+H).

Sources & evidence

ORD record
ord-a255db5d161c4ece86bb3aefa9bc2254
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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