Sodium Bicarbonate → HCID 57385599, compound

HRID 1427793Notes

Reaction equation

HRID 1427793 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-68fd23d58d534f4f83a5ef42b3633c5b
Source dataset
uspto-grants-2015_01
Patent number
US08933015B2

Reaction notes

Loading…