Ammonium formate → HCID 57933219, compound

HRID 1433291Notes

Reaction equation

C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:55][Si:56]([C:59]([CH3:62])([CH3:61])[CH3:60])([CH3:58])[CH3:57])[CH2:16][NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([C@@H:39]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[CH2:40][CH2:41][N:42]([CH:46]([CH3:48])[CH3:47])[CH:43]([CH3:45])[CH3:44])[CH:33]=3)=[CH:22][CH:21]=2)=[CH:11][C:10]=1[NH:63][S:64]([CH3:67])(=[O:66])=[O:65])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[Si:56]([O:55][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([NH:63][S:64]([CH3:67])(=[O:65])=[O:66])[CH:11]=1)[CH2:16][NH:17][CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([C@@H:39]([C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)[CH2:40][CH2:41][N:42]([CH:46]([CH3:48])[CH3:47])[CH:43]([CH3:45])[CH3:44])[CH:33]=2)=[CH:24][CH:25]=1)([C:59]([CH3:62])([CH3:60])[CH3:61])([CH3:58])[CH3:57]

Participants

Conditions

Temperature: 90 °C

Procedure

N-[2-(benzyloxy)-5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[(2-{4-[(5-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}pentyl)oxy]phenyl}ethyl)amino]ethyl}phenyl]methanesulfonamide (Preparation 60, 350 mg, 0.37 mmol) was dissolved in ethanol (10 ml) and ammonium formate (1.0 g, 16 mmol) and 20% palladium hydroxide on carbon (250 mg) were added and heated to 90° C. for 1 hour. Reaction mixture was then cooled and filtered through Arbocel and the solvent removed in vacuo to furnish the title compound as a colourless oil, 250 mg.

Workup

customReaction mixture
temperaturewas then cooled
filtrationfiltered through Arbocel
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-9fe9fb2511d44c169c242e7275c1d2a8
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612084B2

Reaction notes

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