Sodium Bicarbonate → HCID 57385348, compound

HRID 1427791Notes

Reaction equation

HRID 1427791 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:8]=[C:9]([CH:49]=[CH:50][CH:51]=1)[CH2:10][C@@H:11]1[NH:36][C:35](=[O:37])[C@H:34]([CH:38]([CH3:40])[CH3:39])[NH:33][C:32](=[O:41])[CH2:31][C@H:30]([O:42][CH3:43])[CH2:29][CH2:28][CH:27]=[CH:26][C:25]2=[CH:44][C:21](=[CH:22][CH:23]=[CH:24]2)[C@@H:20]([CH3:45])[O:19][C:18](=[O:46])[C@H:17]2[NH:47][N:13]([CH2:14][CH2:15][CH2:16]2)[C:12]1=[O:48])(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:49]=[CH:50][CH:51]=1)[CH2:10][C@@H:11]1[NH:36][C:35](=[O:37])[C@H:34]([CH:38]([CH3:39])[CH3:40])[NH:33][C:32](=[O:41])[CH2:31][C@H:30]([O:42][CH3:43])[CH2:29][CH2:28][CH:27]=[CH:26][C:25]2=[CH:44][C:21](=[CH:22][CH:23]=[CH:24]2)[C@@H:20]([CH3:45])[O:19][C:18](=[O:46])[C@H:17]2[NH:47][N:13]([CH2:14][CH2:15][CH2:16]2)[C:12]1=[O:48]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 71225351HCID 71225351, compound

Product 1

HCID 57385348HCID 57385348, compoundYield 122.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (E)-(2R,5S,11S,14S,18R)-11-[3-(tert-butyl-dimethyl-silanyloxy)-benzyl]-14-isopropyl-18-methoxy-2-methyl-3-oxa-9,12,15,28-tetraaza-tricyclo[21.3.1.1*5,9*]octacosa-1(26),21,23(27),24-tetraene-4,10,13,16-tetraone (54 mg, 0.072 mmol) in anhydrous tetrahydrofuran (10 mL) was cooled over an ice bath before addition of tetra-N-butylammonium fluoride (1 M, 108 μL, 0.108 mmol). The reaction mixture was stirred at room temperature for 1.5 hours and then saturated aqueous sodium bicarbonate solution (20 mL) was added. The mixture was extracted with ethyl acetate (3×15 mL). The extract was dried over anhydrous sodium sulfate, filtered and evaporated to give a brown gum (56 mg). The gum was purified by silica gel chromatography using ethyl acetate/iso-hexanes 3:1 to give a colourless gum (23 mg) which crystallised on standing. The solid was further purified by preparative thin layer chromatography on silica plates using ethyl acetate to yield the title compound (12 mg, 26%) as a colourless solid. 1H NMR (300 MHz, CDCl3) δ0.97 (d, J=6.9 Hz, 3H), 0.98 (d, J=6.7 Hz, 3H), 1.63 (d, J=6.5 Hz, 3H), 1.66-1.82 (m, 5H), 1.85-2.04 (m, 3H), 2.16-2.35 (m, 1H), 2.53-2.73 (m, 3H), 2.88 (d, J=6.0 Hz, 2H), 3.43 (s, 3H), 3.47-3.60 (m, 3H), 4.24-4.33 (m, 1H), 4.56 (d, J=11.6 Hz, 1H), 5.59-5.70 (m, 1H), 5.79-5.95 (m, 2H), 5.98-6.12 (m, 1H), 6.69-6.85 (m, 3H), 6.97 (s, 1H), 7.02-7.36 (m, 6H), 8.18 (s, 1H). LCMS (m/z) 635.3 [M+H] Tr=5.42 min.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×15 mL)
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-ecc39b3f36f1418682117d38dee8abd4
Source dataset
uspto-grants-2015_01
Patent number
US08933015B2

Reaction notes

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