1,4-Cyclohexadiene → HCID 11151881, compound

HRID 851925Notes

Reaction equation

HRID 851925 reaction equation
[CH2:1]([O:8][N:9]([CH2:12][CH:13]1[C:18](=[O:19])[N:17]([CH2:20][C:21]([NH:23][CH2:24][CH2:25][CH3:26])=[O:22])[C:16]2[CH:27]=[CH:28][CH:29]=[CH:30][C:15]=2[S:14]1)[CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CC=CCC=1>CCO.[Pd]>[CH2:1]([O:8][N:9]([CH2:12][CH:13]1[C:18](=[O:19])[N:17]([CH2:20][C:21]([NH:23][CH2:24][CH2:25][CH3:26])=[O:22])[C:16]2[CH:27]=[CH:28][CH:29]=[CH:30][C:15]=2[S:14]1)[CH:10]=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH:10]([N:9]([CH2:12][CH:13]1[C:18](=[O:19])[N:17]([CH2:20][C:21]([NH:23][CH2:24][CH2:25][CH3:26])=[O:22])[C:16]2[CH:27]=[CH:28][CH:29]=[CH:30][C:15]=2[S:14]1)[OH:8])=[O:11]

Participants

6

Reactant 2

HCID 123431,4-CyclohexadieneHCID 86600478HCID 86600478, compound

Product 2

HCID 11151881HCID 11151881, compoundHCID 86600478HCID 86600478, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-{2-[(benzyloxy-formyl-amino)-methyl]-3-oxo-2,3-dihydro-benzo[1,4]thiazin-4-yl}-N-propyl-acetamide (0.13 mmol) in 9 ml of EtOH is added Pd/C (10%) (65.6 mg) followed by 1,4-cyclohexadiene (1.29 mL). The reaction mixture is stirred at room temperature for 12 hours and the final product 2-{2-[(formyl-hydroxy-amino)-methyl]-3-oxo-2,3-dihydro-benzo[1.4]thiazin-4-yl}-N-propyl-acetamide is obtained by preparative LC/MS using 1 to 99% ACN (in the absence of TFA) as gradient. MS: (ES+): 338.2 [M+1].

Sources & evidence

ORD record
ord-fa4452e4ae544fc2812c2fb38bbdc1e6
Source dataset
uspto-grants-2007_08
Patent number
US07253164B2

Reaction notes

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