Tributylvinyltin → HCID 136387744, compound

HRID 1924385Notes

Reaction equation

HRID 1924385 reaction equation
I[C:2]1[C:3]2[C:26]3=[CH:27][C:6]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]4[O:37][C:14]([NH:15][C@@H:16]([CH:34]([CH3:36])[CH3:35])[C:17](=[O:33])[N:18]5[CH2:28][C@H:21]([O:22][C:23]3=[N:24][CH:25]=1)[CH2:20][C@H:19]5[C:29]([O:31][CH3:32])=[O:30])=[N:13][N:12]=4)=[CH:5][CH:4]=2.[CH2:38]([Sn](CCCC)(CCCC)C=C)[CH2:39]CC>C1(C)C=CC=CC=1.CCOC(C)=O.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:34]([C@@H:16]1[NH:15][C:14]2[O:37][C:11](=[N:12][N:13]=2)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]2[CH:27]=[C:26]3[C:3](=[CH:4][CH:5]=2)[C:2]([CH:38]=[CH2:39])=[CH:25][N:24]=[C:23]3[O:22][C@H:21]2[CH2:28][N:18]([C@H:19]([C:29]([O:31][CH3:32])=[O:30])[CH2:20]2)[C:17]1=[O:33])([CH3:36])[CH3:35]

Participants

6

Reactant 2

HCID 81998TributylvinyltinHCID 136387745HCID 136387745, compound

Product 1

HCID 136387744HCID 136387744, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a 0.1 M solution of methyl (3R,5S,8S)-22-iodo-8-isopropyl-7-oxo-2,27-dioxa-6,9,11,12,24-pentaazapentacyclo[16.6.2.13,6.110,13.021,25]octacosa-1(24), 10,12,18,20,22,25-heptaene-5-carboxylate (Example 12, Step 2) in dry toluene was added tetrakis(triphenylphosphine)palladium(0) (0.05 eq.). N2 was bubbled through the reaction mixture for 5 minutes and tributylethenylstannane (1.5 eq) was added. The mixture was stirred at 100° C. for 1 h, allowed to cool to RT, diluted with EtOAc and washed with brine. The organic layer was separated, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel (20% to 40% EtOAc/PE) to give the compound as a white solid. MS (ES+) C28H33N5O5 requires: 519. Found: 520 (M+H+).

Workup

  1. customN2 was bubbled through the reaction mixture for 5 minutes
  2. temperatureto cool to RT
  3. washwashed with brine
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel (20% to 40% EtOAc/PE)

Sources & evidence

ORD record
ord-9d122c2df3d14937bc70ff28fa607871
Source dataset
uspto-grants-2012_05
Patent number
US08178520B2

Reaction notes

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