Acetone → HCID 118194677, compound

HRID 1770383Notes

Reaction equation

HRID 1770383 reaction equation
[CH2:1]([C@H:5]1[C@@H:13](C(C)(C)C([O-])=O)[CH2:12][CH2:11][CH2:10][C@H:9]([NH:20][C:21](=[O:31])[C:22]2[C:27]([OH:28])=[C:26]([O:29][CH3:30])[CH:25]=[CH:24][N:23]=2)[C:8](=[O:32])[O:7][C@H:6]1[CH3:33])[CH2:2][CH2:3][CH3:4].[C:34]([O-:37])([O-])=[O:35].[Na+].[Na+].[Na+].[I-].[CH2:42]([O:44][CH2:45][C:46]([O:48][CH2:49]Cl)=[O:47])[CH3:43].[CH3:51][C:52]([CH3:54])=O>>[C:34]([O:37][C@H:13]1[CH2:12][CH2:11][CH2:10][C@H:9]([NH:20][C:21](=[O:31])[C:22]2[C:27]([O:28][CH2:49][O:48][C:46]([CH2:45][O:44][CH2:42][CH3:43])=[O:47])=[C:26]([O:29][CH3:30])[CH:25]=[CH:24][N:23]=2)[C:8](=[O:32])[O:7][C@@H:6]([CH3:33])[C@@H:5]1[CH2:1][CH2:2][CH2:3][CH3:4])(=[O:35])[CH:52]([CH3:54])[CH3:51]

Participants

6

Reactant 5

HCID 180AcetoneHCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 89886406HCID 89886406, compoundHCID 131734630HCID 131734630, compound

Product 1

HCID 118194677HCID 118194677, compoundYield 41%

Conditions

Temperature
45 °C

Procedure

To a solution of (2S,3S,4S,8S)-3-butyl-8-(3-hydroxy-4-methoxypicolinamido)-2-methyl-9-oxooxonan-4-ylisobutyrate (45 mg, 0.097 mmol), Na2CO3 (20.5 mg, 0.194 mmol), and NaI (22.2 mg, 0.145 mmol) in acetone (2.0 mL) was added chloromethyl 2-ethoxyacetate (22.2 mg, 0.145 mmol). The sealed reaction was warmed to 45° C. and stirred for 16 h. The reaction was cooled to room temperature and concentrated under a stream of N2. The resulting residue was purified by flash column chromatography (4 g SiO2, 0→100% EtOAc/hexanes) to afford the title compound (23.2 mg, 0.040 mmol, 41%) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 8.34 (d, J=8.1 Hz, 1H), 8.28 (d, J=5.4 Hz, 1H), 6.95 (d, J=5.4 Hz, 1H), 5.82 (s, 2H), 4.90 (ddd, J=9.1, 5.6, 1.9 Hz, 1H), 4.83 (dq, J=10.0, 6.4 Hz, 1H), 4.62 (ddd, J=10.7, 8.1, 7.1 Hz, 1H), 4.10 (s, 2H), 3.90 (s, 3H), 3.59 (q, J=7.0 Hz, 2H), 2.53 (hept, J=7.0 Hz, 1H), 2.36 (dt, J=13.7, 6.8 Hz, 1H), 2.21-2.03 (m, 2H), 1.87-1.76 (m, 1H), 1.60-1.51 (m, 1H), 1.41-1.32 (m, 5H), 1.32-1.25 (m, 3H), 1.23 (t, J=7.0 Hz, 4H), 1.17 (dd, J=7.0, 0.8 Hz, 7H), 1.05 (ddt, J=15.9, 7.5, 2.2 Hz, 1H), 0.88 (t, J=7.1 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 176.48, 172.33, 170.05, 162.94, 160.18, 145.80, 143.89, 142.32, 109.69, 89.56, 74.52, 73.29, 67.80, 67.19, 56.22, 51.32, 45.49, 34.29, 32.91, 30.88, 28.17, 27.45, 23.30, 19.22, 19.09, 18.94, 18.14, 15.01, 13.88; HRMS-ESI m/z [M+H]+ calcd for: C29H44N2O10, 581.3069; found 581.3073.

Workup

  1. customThe sealed reaction
  2. temperatureThe reaction was cooled to room temperature
  3. concentrationconcentrated under a stream of N2
  4. customThe resulting residue was purified by flash column chromatography (4 g SiO2, 0→100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-60cc34eb24c2482d895708aa23fd723a
Source dataset
uspto-grants-2016_02
Patent number
US09247741B2

Reaction notes

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