Acetic Acid → HCID 91317120, compound

HRID 643089Notes

Reaction equation

HRID 643089 reaction equation
[OH:1][C@H:2]([C@@H:18]([NH:26][C:27](=[O:48])[C@@H:28]([N:33]1[CH2:37][CH2:36][N:35]([CH2:38][C:39]2[N:40]=[C:41]([CH2:44][O:45][CH3:46])[S:42][CH:43]=2)[C:34]1=[O:47])[C@@H:29]([CH3:32])[CH2:30][CH3:31])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:3][NH:4][NH:5][C:6]([C@@H:8]([NH:13][C:14](=[O:17])[O:15][CH3:16])[C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[CH:49](=O)[CH2:50][CH:51]([CH3:53])[CH3:52].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[OH:1][C@H:2]([C@@H:18]([NH:26][C:27](=[O:48])[C@@H:28]([N:33]1[CH2:37][CH2:36][N:35]([CH2:38][C:39]2[N:40]=[C:41]([CH2:44][O:45][CH3:46])[S:42][CH:43]=2)[C:34]1=[O:47])[C@@H:29]([CH3:32])[CH2:30][CH3:31])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:3][N:4]([CH2:49][CH2:50][CH:51]([CH3:53])[CH3:52])[NH:5][C:6]([C@@H:8]([NH:13][C:14](=[O:17])[O:15][CH3:16])[C:9]([CH3:11])([CH3:10])[CH3:12])=[O:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 115523-MethylbutanalHCID 5049666Sodium triacetoxyborohydrideHCID 91599403HCID 91599403, compound

Product 1

HCID 91317120HCID 91317120, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of Example 280A (20 mg, 0.029 mmol) in 1,2-dichloroethane (0.3 mL) was treated with isovaleraldehyde (6.2 μL, 2 equivalents), acetic acid (3.3 μL, 2 equivalents), and sodium triacetoxyborohydride (18.5 mg, 3 equivalents) at 25° C. for 16 hrs. The mixture was partitioned between dichloromethane and saturated sodium bicarbonate. The organic layer was separated, washed with brine, dried over magnesium sulfate, filtered, and the solvents were evaporated. The residue was purified by HPLC reverse phase chromatography using water (0.1% TFA):acetonitrile (95:5) to acetonitrile (100%) to give 8 mg (36%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.78 (dd, J=13.79, 6.43 Hz, 12H), 0.91 (m, 9H), 1.25 (m, 3H), 1.62 (m, 1H), 1.77 (d, J=8.82 Hz, 1H), 2.58 (m, 3H), 2.69 (m, 4H), 2.79 (m, 2H), 3.09 (m, 3H), 3.37 (s, 3H), 3.81 (m, 2H), 3.95 (m, 2H), 4.10 (s, 1H), 4.36 (m, 2H), 4.66 (s, 1H), 7.06 (m, 5H), 7.20 (m, 1H), 7.44 (m, 1H), 8.96 (s, 2H), 9.17 (s, 1H), 9.48 (s, 1H).

Workup

  1. customThe mixture was partitioned between dichloromethane and saturated sodium bicarbonate
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvents were evaporated
  7. customThe residue was purified by HPLC reverse phase chromatography

Sources & evidence

ORD record
ord-a59901dc0b0b458f91534cc0cadf3ffb
Source dataset
uspto-grants-2010_04
Patent number
US07696226B2

Reaction notes

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