HCID 67972521, compound → HCID 70656940, compound

HRID 1911826Notes

Reaction equation

C(OC([NH:11][C@@H:12]([C@H:28]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:13][CH2:14][C:15](=O)[CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1)=O)C1C=CC=CC=1>C(O)C.[Pd]>[Si:36]([O:35][C@H:28]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C@@H:12]1[NH:11][C@H:15]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:25][CH:26]=2)[CH2:14][CH2:13]1)([C:39]([CH3:41])([CH3:42])[CH3:40])([CH3:38])[CH3:37]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the title compound from Step G above (9.00 g, 0.625 mmol) in ethanol (200 ml) was added 3.0 g of 10% Pd/C under argon. The reaction mixture was stirred at 50° C. under a H2 balloon overnight. After filtration and removal of the solvent, 6.0 g (90%) of the title compound was obtained which was directly used for the next step without further purification. 1H NMR (CDCl3, 400 MHz): δ7.89 (d, J=7.9 Hz, 2H), 7.24-7.19 (m, 7H), 4.40 (d, J=7.0 Hz, 1H), 3.82 (s, 3H), 3.26-3.09 (m, 2H), 2.75 (d, J=7.0 Hz, 2H), 1.71-1.63 (m, 2H), 1.33-1.25 (m, 2H), 0.75 (s, 9H), 0.00 (s, 6H). MS: m/z (ESI) 440 (M+1).

Workup

filtrationAfter filtration and removal of the solvent

Sources & evidence

ORD record: ord-203ab2edf11c4fe9bcdf0a2ab0b3200f
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604038B2

Reaction notes

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