Sodium Bicarbonate → HCID 57384590, compound

HRID 1895771Notes

Reaction equation

HRID 1895771 reaction equation
C([Si](C)(C)[O:6][C@@H:7]1[C:30]2=[CH:31][CH:32]=[C:27]([CH:28]=[CH:29]2)[CH:26]=[CH:25][CH2:24][CH2:23][O:22][C:21](=[O:33])[C@H:20]2[NH:34][N:16]([CH2:17][CH2:18][CH2:19]2)[C:15](=[O:35])[C@H:14]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([O:43][Si](C(C)(C)C)(C)C)[CH:38]=2)[NH:13][C:12](=[O:51])[C@H:11]([CH:52]([CH3:54])[CH3:53])[NH:10][C:9](=[O:55])[C@@H:8]1[CH3:56])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)(O)[O-].[Na+]>O1CCCC1>[OH:6][C@@H:7]1[C:30]2=[CH:29][CH:28]=[C:27]([CH:32]=[CH:31]2)[CH:26]=[CH:25][CH2:24][CH2:23][O:22][C:21](=[O:33])[C@H:20]2[NH:34][N:16]([CH2:17][CH2:18][CH2:19]2)[C:15](=[O:35])[C@H:14]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([OH:43])[CH:38]=2)[NH:13][C:12](=[O:51])[C@H:11]([CH:52]([CH3:53])[CH3:54])[NH:10][C:9](=[O:55])[C@@H:8]1[CH3:56]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 71225365HCID 71225365, compound

Product 1

HCID 57384590HCID 57384590, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 8d (90 mg, 0.108 mmol.) in anhydrous tetrahydrofuran (30 ml) was cooled over an ice bath before adding a solution of tetra-n-butylammonium fluoride (1M in tetrahydrofuran, 1.08 ml, 1.08 mmol.). The reaction was warmed to room temperature and stirred for 1 hour before adding saturated sodium bicarbonate solution (25 ml). The mixture was extracted with ethylacetate (2×25 ml). The extract was dried over anhydrous sodium sulfate, filtered and evaporated to give a brown gum. The gum was purified on a silica column eluting with ethyl acetate to yield 8 as a white solid (27 mg) LCMS. (m/z) 607.27 [M+H] Tr=4.21 min 1H NMR δ (300 MHz NMR, CDCl3) 1.12-1.28 (m, 6H), 1.31-1.39 (d, 3H, J=7.1 Hz), 1.44-1.60 (m, 3H), 1.71-2.13 (m, 3H) 2.14-2.28 (m, 1H), 2.38-2.70 (m, 4H), 2.81-2.91 (m, 1H), 2.91-3.08 (m, 1H), 3.61-3.70 (d, 1H), 4.12-4.21 (m, 1H), 4.32-4.46 (m, 2H), 4.81-4.89 (s, 1H) 5.07-5.18 (q, 1H, J=6.5 Hz), 5.90-6.05 (m, 1H) 6.15-6.33 (m, 3H) 6.37-6.44 (d, 1H) 6.61-6.70 (m, 1H) 6.95-7.72 (m, 7H) 7.80-8.05 (bs, 1H).

Workup

  1. extractionThe mixture was extracted with ethylacetate (2×25 ml)
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto give a brown gum
  6. customThe gum was purified on a silica column
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-8023ff3ba0df4f9595505999bdc16a33
Source dataset
uspto-grants-2013_08
Patent number
US08513184B2

Reaction notes

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