Sodium Chloride → HCID 131734757, compound

HRID 1776113Notes

Reaction equation

HRID 1776113 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][C@H:8]1[CH2:16][CH2:15][CH2:14][C@H:13]([CH2:17][CH2:18]O)[C@@H:12]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@H:11]([CH3:27])[O:10][C:9]1=[O:28])([CH3:4])([CH3:3])[CH3:2].[N+:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[Se:39]C#N)([O-:32])=[O:31].C(P(CCCC)CCCC)CCC.[Na+].[Cl-]>C1COCC1>[C:1]([O:5][C:6](=[O:29])[NH:7][C@H:8]1[CH2:16][CH2:15][CH2:14][C@H:13]([CH2:17][CH2:18][Se:39][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N+:30]([O-:32])=[O:31])[C@@H:12]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@H:11]([CH3:27])[O:10][C:9]1=[O:28])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 13831Tributylphosphine2×HCID 1039312-Nitrophenyl selenocyanate2×HCID 117982168HCID 117982168, compound

Product 1

HCID 131734757HCID 131734757, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl((3S,7R,8R,9S)-7-(2-hydroxyethyl)-9-methyl-2-oxo-8-phenoxyoxonan-3-yl)carbamate (227 mg, 0.557 mmol) in anhydrous THF (5.6 mL) at 0° C. (ice water bath) were added 1-nitro-2-selenocyanatobenzene (177 mg, 0.780 mmol) and tributylphosphine (223 μl, 0.891 mmol). The resulting solution was stirred for 3 h and then treated with additional 1-nitro-2-selenocyanatobenzene and tributylphospine (53 mg and 67 μL, respectively). The reaction was stirred for an additional 1 h, then poured into 20 mL sat. NaCl solution and extracted with 3×20 mL EtOAc. The organic extracts were combined, dried over MgSO4, filtered, and concentrated to provide a brown oil, which was purified by column chromatography on SiO2 (2→20% acetone/hexanes) to provide the title compound as a bright yellow solid (294 mg, 89%): 1H NMR (400 MHz, CDCl3) δ 8.24 (dt, J=8.2, 1.0 Hz, 1H), 7.36-7.19 (m, 5H), 7.00-6.92 (m, 1H), 6.92-6.84 (m, 2H), 5.16-4.98 (m, 2H), 4.21 (t, J=8.5 Hz, 2H), 3.05-2.76 (m, 2H), 2.30 (dt, J=13.2, 6.7 Hz, 1H), 1.94 (tdq, J=28.6, 14.1, 8.4, 6.4 Hz, 3H), 1.78-1.64 (m, 2H), 1.60 (d, J=4.5 Hz, 1H), 1.45 (s, 9H), 1.30 (d, J=6.5 Hz, 3H), 1.27-1.13 (m, 2H); 13C NMR (101 MHz, CDCl3) δ 173.23, 159.12, 154.89, 146.86, 133.45, 133.21, 129.76, 128.95, 126.41, 125.29, 121.34, 115.33, 80.99, 79.97, 74.59, 52.99, 43.60, 34.00, 29.99, 28.58, 28.33, 24.24, 19.15, 18.29; ESIMS m/z 593.2 ([M+Na]+).

Workup

  1. stirringThe reaction was stirred for an additional 1 h
  2. extractionextracted with 3×20 mL EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide a brown oil, which
  7. customwas purified by column chromatography on SiO2 (2→20% acetone/hexanes)

Sources & evidence

ORD record
ord-acc45b4fd0534dff8accb72111369d26
Source dataset
uspto-grants-2016_02
Patent number
US09265253B2

Reaction notes

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