Hydrochloric Acid → HCID 68455361, compound

HRID 2356055Notes

Reaction equation

HRID 2356055 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:29][C:30](=[O:51])[C:31]2[CH:36]=[CH:35][C:34]([C:37]3[CH:50]=[CH:49][C:40]4[N:41]([CH2:45][CH2:46][CH2:47][CH3:48])[C:42](=[O:44])[NH:43][C:39]=4[CH:38]=3)=[CH:33][CH:32]=2)(=[O:28])=[O:27])=[CH:22][C:21]=1[N+:52]([O-:54])=[O:53])[CH2:11][S:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>C1COCC1>[CH2:45]([N:41]1[C:40]2[CH:49]=[CH:50][C:37]([C:34]3[CH:35]=[CH:36][C:31]([C:30]([NH:29][S:26]([C:23]4[CH:24]=[CH:25][C:20]([NH:19][C@@H:10]([CH2:11][S:12][C:13]5[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=5)[CH2:9][OH:8])=[C:21]([N+:52]([O-:54])=[O:53])[CH:22]=4)(=[O:28])=[O:27])=[O:51])=[CH:32][CH:33]=3)=[CH:38][C:39]=2[NH:43][C:42]1=[O:44])[CH2:46][CH2:47][CH3:48]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 68454211HCID 68454211, compound

Product 1

HCID 68455361HCID 68455361, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of Example 177A (40 mg, 0.05 mmol) and 1M tetrabutylammonium fluoride in THF (130 uL, 0.13 mmol) in THF (3 mL) at room temperature was stirred for 3 hours, treated with 1M HCl (10 mL), and extracted with 5% methanol in ethyl acetate (3×20 mL). The combined extracts were washed with brine (5 mL), dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 20% methanol/ethyl acetate to provide the desired product. MS (ESI) m/e 674, 676 (M−H)−, (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 0.91 (t, 3H), 1.30 (q, 2H), 1.59 (tt, 2H), 3.28 (t, 2H), 3.67 (m, 1H), 3.80 (t, 2H), 3.92 (m, 2H), 5.21 (t, 1H), 6.83 (d, 1H), 7.21 (m, 3H), 7.29 (td, 2H), 7.38 (dd, 2H), 7.55 (d, 2H), 7.80 (dd, 1H), 7.94 (d, 2H), 7.95 (d, 1H), 8.41 (d, 1H), 8.49 (d, 1H), 10.90 (s, 1H).

Workup

  1. extractionextracted with 5% methanol in ethyl acetate (3×20 mL)
  2. washThe combined extracts were washed with brine (5 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography on silica gel with 20% methanol/ethyl acetate

Sources & evidence

ORD record
ord-8db6505f6bcb4cecae6fa9b3ffcfe832
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

Loading…