HCID 86762144, compound → HCID 86762143, compound

HRID 1907405Notes

Reaction equation

HRID 1907405 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C@:11]12[O:19][CH2:18][CH2:17][C@H:16]1[CH2:15][S:14][C:13]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[N:12]2>CO.[Pd]>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C@:11]23[O:19][CH2:18][CH2:17][C@H:16]2[CH2:15][S:14][C:13]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[N:12]3)[CH:4]=1

Participants

4

Reactant 1

HCID 86762144HCID 86762144, compound

Product 1

HCID 86762143HCID 86762143, compoundYield 104.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (±)-tert-butyl (4aR,7aR)-7a-(2-fluoro-5-nitrophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-ylcarbamate (31 mg, 0.078 mmol) in methanol (3.9 mL) was added 10% Pd/C (17 mg), and the reaction mixture was stirred at rt under a hydrogen atmosphere for 2 h. The reaction mixture was filtered through a pad of Celite and concentrated directly to give the title compound as a colorless oil (30 mg, 99%). 1H NMR (500 MHz, CDCl3) δ 6.87 (2H, m), 6.63 (1H, m), 4.17 (1H, m), 4.09 (1H, m), 3.35 (1H, m), 3.05 (1H, m), 2.89 (1H, m), 2.35 (1H, m), 2.23 (1H, m), and 1.51 (9H, m). MS (M+H)+: 368.2.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationconcentrated directly

Sources & evidence

ORD record
ord-f4cf50af84ed4f4b87320df5cd73de6b
Source dataset
uspto-grants-2013_12
Patent number
US08598161B2

Reaction notes

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