Tri(butyl)vinyltin → HCID 66782652, compound

HRID 1095296Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[O:12][C@H:13]2[CH2:17][N:16]([C:18](=[O:37])[C@H:19]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)[NH:20][C:21]([O:23][CH2:24][C:25]([CH3:30])([CH3:29])[CH2:26][CH:27]=[CH2:28])=[O:22])[C@H:15]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:14]2)=[CH:4][C:3]=1[O:43][CH3:44].[CH2:45](C([Sn])=C(CCCC)CCCC)[CH2:46]CC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:31]1([C@H:19]([NH:20][C:21]([O:23][CH2:24][C:25]([CH3:30])([CH3:29])[CH2:26][CH:27]=[CH2:28])=[O:22])[C:18]([N:16]2[CH2:17][C@H:13]([O:12][C:9]3[C:10]4[C:5](=[CH:4][C:3]([O:43][CH3:44])=[C:2]([CH:45]=[CH2:46])[CH:11]=4)[CH:6]=[CH:7][N:8]=3)[CH2:14][C@H:15]2[C:38]([O:40][CH2:41][CH3:42])=[O:39])=[O:37])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

Conditions

Temperature: 105 °C

Procedure

A solution of the product from Step 5 (1.02 g, 1.51 mmol) in PhMe (30 mL) was degassed for 30 minutes by bubbling nitrogen. Tri-n-butylvinyltin (533 μL, 1.81 mmol) and tetrakis(triphenylphosphine)palladium (175 mg, 0.151 mmol) were added, and the reaction mixture was heated to 105° C. for 3 hours, then cooled to RT for 18 hours. The volatiles were evaporated, and the residue was purified by chromatography on silica (20-50% EtOAc/hexane) to afford the title compound (820 mg) as a foam. LRMS ESI+ (M+H)+622.5.

Workup

customby bubbling nitrogen
temperaturecooled to RT for 18 hours
customThe volatiles were evaporated
customthe residue was purified by chromatography on silica (20-50% EtOAc/hexane)

Sources & evidence

ORD record: ord-15209242b7604a57b24c774a1f26d943
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138164B2

Reaction notes

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