Acetic Acid → HCID 91247094, compound

HRID 643070Notes

Reaction equation

HRID 643070 reaction equation
[CH2:1]([C@H:8]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C@@H:9]([OH:25])[CH2:10][NH:11][NH:12][C:13](=[O:24])[C@@H:14]([NH:19][C:20]([O:22][CH3:23])=[O:21])[C:15]([CH3:18])([CH3:17])[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[CH3:38][C:39]1[O:43][N:42]=[C:41]([C:44]2[S:45][CH:46]=[C:47]([CH:49]=O)[N:48]=2)[CH:40]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.ClCCl.C(=O)(O)[O-].[Na+]>[CH2:1]([C@H:8]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C@@H:9]([OH:25])[CH2:10][N:11]([CH2:49][C:47]1[N:48]=[C:44]([C:41]2[CH:40]=[C:39]([CH3:38])[O:43][N:42]=2)[S:45][CH:46]=1)[NH:12][C:13](=[O:24])[C@@H:14]([NH:19][C:20]([O:22][CH3:23])=[O:21])[C:15]([CH3:18])([CH3:17])[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 87540180HCID 87540180, compoundHCID 90787766HCID 90787766, compound

Product 1

HCID 91247094HCID 91247094, compoundYield 99.2%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
25 °C

Procedure

A solution of Example 19A (0.4 g, 0.86 mmol) in dichloroethane (5.7 mL) was treated with acetic acid (99 μL, 2 equivalents), 2-(5-methyl-3-isoxazolyl)thiazole 4-carboxaldehyde (0.199 g, 1.2 equivalents), and sodium triacetoxyborohydride (0.545 g, 3 equivalents) and stirred at 25° C. for 16 hrs. The mixture was diluted with dichloromethane and saturated sodium bicarbonate. The organic layer was separated, washed with brine, dried over magnesium sulfate, filtered and the solvents were evaporated. The crude residue was purified by HPLC reverse phase chromatography using water (0.1% trifluoroacetic acid):acetonitrile (95:5) to acetonitrile (100%) to give 0.55 g (60%) of the title compound.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvents were evaporated
  6. customThe crude residue was purified by HPLC reverse phase chromatography

Sources & evidence

ORD record
ord-22ccfe0b6d7c4d5e9deaf40ead465d6a
Source dataset
uspto-grants-2010_04
Patent number
US07696226B2

Reaction notes

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