Stannane, hydroxytrimethyl- → HCID 86684666, compound

HRID 1504359Notes

Reaction equation

HRID 1504359 reaction equation
[N:1]([CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C@H:14]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:15]([O:17]C)=[O:16])=[CH:9][CH:8]=1)=[N+:2]=[N-:3].[OH-].C[Sn+](C)C>ClCCCl>[N:1]([CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][C@H:14]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:15]([OH:17])=[O:16])=[CH:11][CH:12]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 11217597Stannane, hydroxytrimethyl-HCID 86684664(S)-Methyl 3-(4-(2-azidoethoxy)phenyl)-2-((tert-butoxycarbonyl)amino)propanoate

Product 1

HCID 86684666HCID 86684666, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2A (1.46 g, 4.0 mmol) was dissolved in 1,2-dichloroethane (20 mL) and after addition of trimethyltin hydroxide (2.17 g, 12.0 mmol), the mixture was heated at 80° C. until TLC analysis indicated a complete reaction. After completion of the reaction, the mixture was concentrated in vacuo, and the residue was taken up in EtOAc (80 mL). The organic layer was washed with aqueous HCl (5%) (3×50 mL). The organic layer was then washed with brine and dried over Na2SO4. After removal of the solvent in vacuo, the residue was purified by flash column chromatography (SiO2, step-wise gradient from 2-20% MeOH in CH2Cl2) to give 3A (0.98 g, 70%) as a white solid. 1H NMR (600 MHz, CDCl3): δ 7.11 (2H, d, J=8.4 Hz), 6.86 (2H, d, J=8.4 Hz), 4.94 (1H, d, J=7.2 Hz), 4.53-4.60 (1H, m), 4.13 (2H, t, J=5.4 Hz), 3.58 (2H, t, J=5.4 Hz), 3.14 (1H, dd, J=13.8, 5.4 Hz), 3.04 (1H, dd, J=13.8, 5.4 Hz), 1.43 (9H, s); 13C NMR (150 MHz, CDCl3): δ 157.3, 155.5, 130.5, 128.8, 114.7, 80.2, 66.9, 54.7, 50.1, 37.0, 28.3; MS (ESI, m/z): 373 (M+Na)+.

Workup

  1. customa complete reaction
  2. customAfter completion of the reaction
  3. concentrationthe mixture was concentrated in vacuo
  4. washThe organic layer was washed with aqueous HCl (5%) (3×50 mL)
  5. washThe organic layer was then washed with brine
  6. dry with materialdried over Na2SO4
  7. customAfter removal of the solvent in vacuo
  8. customthe residue was purified by flash column chromatography (SiO2, step-wise gradient from 2-20% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-3c27937dbfc14297b107b2d80773f5c6
Source dataset
uspto-grants-2015_12
Patent number
US09212381B2

Reaction notes

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