HCID 58746442, compound → HCID 58746877, compound

HRID 724647Notes

Reaction equation

HRID 724647 reaction equation
[C:1]([N:5]1[C:9](=[O:10])[CH:8]=[C:7]([C:11]2[CH:28]=[CH:27][C:14]([CH2:15][C:16]3([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:20][CH2:19][C:18](=[O:21])[NH:17]3)=[CH:13][CH:12]=2)[S:6]1(=[O:30])=[O:29])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([N:5]1[C:9](=[O:10])[CH2:8][CH:7]([C:11]2[CH:28]=[CH:27][C:14]([CH2:15][C:16]3([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:20][CH2:19][C:18](=[O:21])[NH:17]3)=[CH:13][CH:12]=2)[S:6]1(=[O:30])=[O:29])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 58746442HCID 58746442, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58746877HCID 58746877, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl 2-[4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)benzyl]-5-oxopyrrolidine-2-carboxylate (24 mg, 0.055 mmol) was dissolved in ethanol (2.5 mL) and 10% Pd/C (10 mg, 0.09 mmol) was added. Hydrogen was added to a Parr shaker (58 psi) and shaken overnight. Purification by preparative LCMS gave the desired product as a colorless glass (23 mg, 95%). 1H NMR (400 MHz, CD3OD): δ 7.42 (d, J=8.2 Hz, 2H), 7.32 (d, J=8.2 Hz, 2H), 5.12 (t, J=8.9 Hz, 1H), 4.20 (q, J=7.2 Hz, 2H), 3.30 (m, 2H), 3.22 (d, J=13.6 Hz, 1H), 3.13 (d, J=13.6 Hz, 1H), 2.38 (m, 1H), 2.21 (m, 2H), 1.92 (m, 1H), 1.61 (s, 9H), 1.28 (t, J=7.0 Hz, 3H); LCMS found for C21H29N2O6S (M+H)+: m/z=437.

Workup

  1. customPurification by preparative LCMS

Sources & evidence

ORD record
ord-0b6101d6e55741acbf022acc4b1ed293
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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