HCID 136403660, compound → HCID 136403663, compound

HRID 494511Notes

Reaction equation

C([O:8][C:9]1[CH:37]=[CH:36][C:12]2[NH:13][C:14]([C:19]3[C:20](=[O:35])[C:21]([CH2:31][CH2:32][CH2:33][CH3:34])([CH3:30])[C:22]4[C:27]([C:28]=3[OH:29])=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:15][S:16](=[O:18])(=[O:17])[C:11]=2[CH:10]=1)C1C=CC=CC=1>O1CCCC1.[Pd]>[CH2:31]([C:21]1([CH3:30])[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28]([OH:29])=[C:19]([C:14]2[NH:13][C:12]3[CH:36]=[CH:37][C:9]([OH:8])=[CH:10][C:11]=3[S:16](=[O:18])(=[O:17])[N:15]=2)[C:20]1=[O:35])[CH2:32][CH2:33][CH3:34]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of Example 27G (1.00 g, 1.94 mmol) in tetrahydrofuran (40 mL) was treated with 10% palladium on carbon (0.100 g, 10% weight) and stirred at 25° C. under a hydrogen balloon for 72 hours. The vessel was purged with nitrogen gas and the mixture was filtered through celite. The filtrate was concentrated in vacuo to give the title compound (0.824 g, 99%). 1H NMR (300 MHz, DMSO-d6): δ ppm 0.54 (m, 1 H) 0.69 (m, 3 H) 0.86 (m, 1 H) 1.10 (m, 2 H) 1.56 (m, 3 H) 2.14 (m, 2 H) 7.18 (m, 2 H) 7.56 (m, 2 H) 7.76 (m, 2 H) 8.16 (m, 1 H) 10.40 (m, 1 H) 13.68 (m, 1 H). MS (ESI−) m/z 425 (M−H)−.

Workup

customThe vessel was purged with nitrogen gas
filtrationthe mixture was filtered through celite
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-f17b15b6f2994c60a87264949bdaad01
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538105B2

Reaction notes

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