Sodium Bicarbonate → HCID 57385599, compound

HRID 1895804Notes

Reaction equation

HRID 1895804 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:8]=[C:9]([CH:46]=[CH:47][CH:48]=1)[CH2:10][C@@H:11]1[NH:34][C:33](=[O:35])[C@H:32]([CH:36]([CH3:38])[CH3:37])[NH:31][C:30](=[O:39])[C@H:29]([CH3:40])[C@H:28]([O:41][CH3:42])[CH2:27][CH2:26][CH:25]=[CH:24][CH2:23][CH2:22][CH2:21][CH2:20][O:19][C:18](=[O:43])[C@H:17]2[NH:44][N:13]([CH2:14][CH2:15][CH2:16]2)[C:12]1=[O:45])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C(=O)(O)[O-].[Na+]>O1CCCC1>[OH:6][C:7]1[CH:8]=[C:9]([CH:46]=[CH:47][CH:48]=1)[CH2:10][C@@H:11]1[NH:34][C:33](=[O:35])[C@H:32]([CH:36]([CH3:38])[CH3:37])[NH:31][C:30](=[O:39])[C@H:29]([CH3:40])[C@H:28]([O:41][CH3:42])[CH2:27][CH2:26][CH:25]=[CH:24][CH2:23][CH2:22][CH2:21][CH2:20][O:19][C:18](=[O:43])[C@H:17]2[NH:44][N:13]([CH2:14][CH2:15][CH2:16]2)[C:12]1=[O:45]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 67960560HCID 67960560, compound

Product 1

HCID 57385599HCID 57385599, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of (E)-(3S,6S,9R,10R,21S)-3-[3-(tert-butyl-dimethyl-silanyloxy)-benzyl]-6-isopropyl-10-methoxy-9-methyl-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacos-13-ene-2,5,8,20-tetraone in anhydrous tetrahydrofuran (15 mL) was cooled to 0° C. under a nitrogen atmosphere before adding a solution of tetra-N-butylammonium fluoride in tetrahydrofuran (1 M, 0.6 mL, 0.6 mmol). The reaction mixture was allowed to warm to room temperature and was then stirred for 1.5 hours. The reaction mixture was treated with a saturated sodium bicarbonate solution (25 mL) and extracted with ethyl acetate (2×20 mL). The extract was dried over anhydrous sodium sulfate, filtered and evaporated to give a brown gum (73 mg), which was purified by silica gel chromatography using ethyl acetate/iso-hexanes 1:1 then ethyl acetate/iso-hexanes 3:1 to give a colourless gum (22 mg). The gum was further purified by preparative thin layer chromatography using ethyl acetate to yield the title product (9 mg, 12%) as a colourless solid. 1H NMR (300 MHz, CD3CN) δ0.94 (d, J=6.5 Hz, 3H), 0.96 (d, J=6.0 Hz, 3H), 1.22-1.45 (m, 3H), 1.28 (d, J=7.4 Hz, 3H), 1.50-1.70 (m, 5H), 1.76-2.08 (m, 7H), 2.47-2.60 (m, 1H), 2.68-2.92 (m, 2H), 2.82 (d, J=6.3 Hz, 1H), 3.21-3.29 (m, 2H), 3.32-3.65 (m, 1H), 3.45 (s, 3H), 4.00-4.37 (m, 4H), 5.10-5.38 (m, 2H), 5.40-5.52 (m, 1H), 6.59-6.70 (m, 2H), 6.78-6.92 (m, 2H), 7.09 (t, J=7.8 Hz, 1H), 7.16 (d, J=9.1 Hz, 1H), 7.80 (s, 1H). LCMS (m/z) 601.4 [M+H] Tr=4.41 min.

Workup

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-dd51ce0614b2496fa25281b1d77bd061
Source dataset
uspto-grants-2013_08
Patent number
US08513184B2

Reaction notes

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