Sodium Bicarbonate → HCID 57384850, compound

HRID 1427765Notes

Reaction equation

HRID 1427765 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][CH:23]=[CH: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.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.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][CH:23]=[CH: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 71225614HCID 71225614, compound

Product 1

HCID 57384850HCID 57384850, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of 11b (38 mg, 0.053 mmol.) in anhydrous tetrahydrofuran (10 ml) was cooled to 0° C. under a nitrogen atmosphere before adding a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (265 ul, 0.265 mmol.). The reaction mixture was warmed to room temperature and was stirred under a nitrogen atmosphere for 2.5 hours. The reaction mixture was then treated with saturated aqueous sodium bicarbonate solution (20 ml) and the subsequent mixture was extracted with ethyl acetate (3×15 ml). The combined extract was dried over sodium sulfate, filtered and evaporated. The residue was purified on a silica column eluting with 50% ethyl acetate, 50% hexane then 100% ethyl acetate to yield 11 as a colourless solid (15 mg, 47%). 1H NMR δ (300 MHz NMR, CDCl3) 0.81-0.92 (m, 3H) 0.93-1.01 (m, 4H), 1.34-1.39 (d, 3H, J=7.4 Hz), 1.45-2.10 (m, 6H), 2.18-2.20 (s, 1H), 2.38-2.53 (m, 2H), 2.55-2.71 (m, 2H), 2.75-2.92 (m, 2H), 3.18-3.30 (m, 2H), 3.51-3.53 (s, 3H), 3.54-3.60 (d, 1H, J=12.5 Hz), 4.09-4.40 (m, 4H), 4.50-4.60 (d, 1H, J=12.7 Hz), 5.43-5.69 (m, 3H), 5.91-6.00 (m, 3H), 6.51-6.58 (d, 1H, J=7.4 Hz), 6.68-6.78 (m, 2H), 6.80-6.90 (d, 1H J=8.7 Hz), 7.05-7.12 (t, 1H, J=7.7), 7.37-7.45 (d, 1H, J=9.6), 8.15-8.38 (bs, 1H). LCMS (m/z) 599.36 [M+H] Tr=4.59 min.

Workup

  1. extractionthe subsequent mixture was extracted with ethyl acetate (3×15 ml)
  2. extractionThe combined extract
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified on a silica column
  7. washeluting with 50% ethyl acetate, 50% hexane

Sources & evidence

ORD record
ord-36b204891d184c66b4bcfbb4449405d1
Source dataset
uspto-grants-2015_01
Patent number
US08933015B2

Reaction notes

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