HCID 131729370, compound → HCID 66649435, compound

HRID 420291Notes

Reaction equation

HRID 420291 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C@H:18]2[C@H:26]3[C@@H:22]([N:23]([CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([CH3:38])([CH3:37])[CH3:36])[CH:30]=4)[C:24](=[O:27])[O:25]3)[CH2:21][S:20](=[O:40])(=[O:39])[CH2:19]2)=[CH:13][C:12]=1[F:41])C1C=CC=CC=1>C1COCC1.CO.[Pd]>[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C@H:18]2[C@H:26]3[C@@H:22]([N:23]([CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([CH3:37])([CH3:38])[CH3:36])[CH:30]=4)[C:24](=[O:27])[O:25]3)[CH2:21][S:20](=[O:39])(=[O:40])[CH2:19]2)=[CH:13][C:12]=1[F:41]

Participants

4

Reactant 1

HCID 131729370HCID 131729370, compound

Product 1

HCID 66649435HCID 66649435, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of {4-[(3aR,7S,7aS)-3-(3-tert-butyl-benzyl)-2,5,5-trioxo-octahydro-1-oxa-5lambda*6*-thia-3-aza-inden-7-ylmethyl]-2-fluoro-phenyl}-carbamic acid benzyl ester (9.6 g, 15.8 mmol) in THF-MeOH 1:2 (150 mL) was hydrogenated over 10% Pd/C (0.7 g) for 4 h at 45° C. and 1 bar. The catalyst was filtered off over Celite and the filtrate is evaporated to provide the title compound as a colorless solid: TLC (toluene-EtOAc 3:1) Rf=0.26; UPLC RtD=1.596 min; ESIMS [M+NH4]+=478; 1H NMR (600 MHz, DMSO-d6): δ 7.38 (s, 1H), 7.32 (d, 1H), 7.27 (t, 1H), 7.13 (d, 1H), 6.83 (d, 1H), 6.69 (m, 2H), 5.02 (s, 2H), 4.42 (d, 1H), 4.22 (d, 1H), 4.11 (t, 1H), 3.67 (m, 2H), 3.46 (t, 1H), 3.01 (m, 2H), 2.79 (dd, 1H), 2.44 (m, 2H), 1.26 (s, 9H).

Workup

  1. filtrationThe catalyst was filtered off over Celite
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-dc48bb32423a477994c30854d91508c7
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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