Sodium Iodide → HCID 89886400, compound

HRID 1627056Notes

Reaction equation

HRID 1627056 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][CH:36]=1)[O:5][C@H:6]1[C@H:14]([CH3:15])[O:13][C:12](=[O:16])[C@@H:11]([NH:17][C:18](=[O:28])[C:19]2[C:24]([OH:25])=[C:23]([O:26][CH3:27])[CH:22]=[CH:21][N:20]=2)[CH2:10][O:9][CH2:8][C@@H:7]1[O:29][CH2:30][CH:31]([CH3:33])[CH3:32].C([O-])([O-])=O.[Na+].[Na+].[Na+].[I-].[CH2:45]([O:47][CH2:48][C:49]([O:51][CH2:52]Cl)=[O:50])[CH3:46]>CC(C)=O>[CH2:45]([O:47][CH2:48][C:49]([O:51][CH2:52][O:25][C:24]1[C:19]([C:18](=[O:28])[NH:17][C@H:11]2[CH2:10][O:9][CH2:8][C@H:7]([O:29][CH2:30][CH:31]([CH3:32])[CH3:33])[C@@H:6]([O:5][C:4]3[CH:34]=[CH:35][CH:36]=[C:2]([Cl:1])[CH:3]=3)[C@H:14]([CH3:15])[O:13][C:12]2=[O:16])=[N:20][CH:21]=[CH:22][C:23]=1[O:26][CH3:27])=[O:50])[CH3:46]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 89886402HCID 89886402, compoundHCID 89886406HCID 89886406, compound

Product 1

HCID 89886400HCID 89886400, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of N-((3S,7S,8S,9S)-8-(3-chlorophenoxy)-7-isobutoxy-9-methyl-2-oxo-1,5-dioxonan-3-yl)-3-hydroxy-4-methoxypicolinamide (85 mg, 0.163 mmol) in acetone (2.0 mL) was added Na2CO3 (34.5 mg, 0.325 mmol), NaI (4.87 mg, 0.033 mmol), and chloromethyl 2-ethoxyacetate (37.2 mg, 0.244 mmol). The reaction was warmed to 45° C. and stirred for 16 h. The reaction was then concentrated and the residue purified by flash chromatography (SiO2; EtOAc/Hexanes) to give the title compound as a white foam (72.2 mg, 69.5%): 1H NMR (400 MHz, CDCl3) δ 8.56 (d, J=8.0 Hz, 1H), 8.29 (d, J=5.4 Hz, 1H), 7.17 (t, J=8.2 Hz, 1H), 7.04 (t, J=2.2 Hz, 1H), 6.96 (d, J=5.4 Hz, 1H), 6.95-6.87 (m, 2H), 5.82 (s, 2H), 5.23-5.06 (m, 2H), 4.25 (t, J=9.1 Hz, 1H), 4.10 (s, 2H), 3.91 (s, 4H), 3.82 (dd, J=11.8, 5.3 Hz, 1H), 3.71 (dd, J=11.1, 7.4 Hz, 1H), 3.59 (q, J=7.0 Hz, 2H), 3.37 (ddd, J=8.9, 7.4, 1.6 Hz, 1H), 3.29 (dd, J=8.8, 6.3 Hz, 1H), 3.15 (dd, J=8.8, 6.4 Hz, 1H), 1.67-1.51 (m, 2H), 1.39 (d, J=6.3 Hz, 3H), 1.23 (t, J=7.0 Hz, 3H), 0.68 (dd, J=18.4, 6.7 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 170.88, 170.06, 163.23, 160.17, 145.87, 143.98, 141.92, 134.59, 129.98, 121.38, 116.68, 114.41, 109.87, 89.44, 83.42, 82.64, 78.00, 74.36, 74.08, 72.30, 67.80, 67.20, 56.25, 52.32, 28.62, 19.16, 19.06, 18.72, 15.01; HRMS-FAB (m/z) [M+H]+ calcd for C30H39ClN2O11, 639.2315; found, 639.2320.

Workup

  1. concentrationThe reaction was then concentrated
  2. customthe residue purified by flash chromatography (SiO2; EtOAc/Hexanes)

Sources & evidence

ORD record
ord-181d4997c2f64c9eaebcc80b6ddc2b50
Source dataset
uspto-grants-2014_07
Patent number
US08785479B2

Reaction notes

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