HCID 68292675, compound → HCID 68291938, compound

HRID 529441Notes

Reaction equation

HRID 529441 reaction equation
[CH2:1]([C@@H:8](/[CH:25]=[CH:26]/[C@H:27]([CH2:44][C:45]([CH3:47])=[CH2:46])[C:28]([N:30]1[C@H:34]2[CH2:35][CH:36]3[C:39]([CH3:41])([CH3:40])[C:33]2([CH2:38][CH2:37]3)[CH2:32][S:31]1(=[O:43])=[O:42])=[O:29])[C:9]([N:11]1[C@H:15]2[CH2:16][CH:17]3[C:20]([CH3:22])([CH3:21])[C:14]2([CH2:19][CH2:18]3)[CH2:13][S:12]1(=[O:24])=[O:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC(O)=O.CCOC(C)=O.[Pd]>[CH2:1]([C@@H:8](/[CH:25]=[CH:26]/[C@H:27]([CH2:44][CH:45]([CH3:47])[CH3:46])[C:28]([N:30]1[C@H:34]2[CH2:35][CH:36]3[C:39]([CH3:40])([CH3:41])[C:33]2([CH2:38][CH2:37]3)[CH2:32][S:31]1(=[O:42])=[O:43])=[O:29])[C:9]([N:11]1[C@H:15]2[CH2:16][CH:17]3[C:20]([CH3:22])([CH3:21])[C:14]2([CH2:19][CH2:18]3)[CH2:13][S:12]1(=[O:24])=[O:23])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 68292675HCID 68292675, compound

Product 1

HCID 68291938HCID 68291938, compoundYield 80.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask was added a solution of (2S,3E,5S)-2-benzyl-1,6-bis((7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3a,6-methano-2,1-benzothiazol-1(3H,4H)-yl)-5-(2-methylprop-2-en-1-yl)hex-3-ene-1,6-dione (67 mg, 0.098 mmol) in AcOH (10.5 mL) and 10% Pd/C (12 mg, 0.011 mmol). The reaction was stirred under an atmosphere of hydrogen (balloon) for 2 hr. The reaction mixture was diluted with EtOAc and filtered. The catalyst was rinsed with EtOAc and the filtrate was concentrated to give (2S,3E,5S)-2-benzyl-1,6-bis((7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3a,6-methano-2,1-benzothiazol-1(3H,4H)-yl)-5-(2-methylpropyl)hex-3-ene-1,6-dione (54 mg, 0.079 mmol, 80% yield) as a syrup. Anal. Calcd. for C32H52N2O6S2 m/z 684.2. found: 685.2 (M+H)+.

Workup

  1. filtrationfiltered
  2. washThe catalyst was rinsed with EtOAc
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-70bca00ff18743348433eb50981fe958
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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