Acetic Acid → HCID 178464122, compound

HRID 351389Notes

Reaction equation

HRID 351389 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[CH2:19][CH2:18][CH:17]([C:20]3[NH:24][C:23]4[C:25]([C:29]([F:32])([F:31])[F:30])=[CH:26][CH:27]=[CH:28][C:22]=4[N:21]=3)[C:16]2=[O:33])[C@H:11]([CH2:34][S:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)(=[O:37])=[O:36])[CH2:10]1.[CH:44](=O)[CH3:45].[C:47](O)(=O)[CH3:48].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CCOC(C)=O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:47]([N:8]([CH2:44][CH3:45])[C@@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[CH2:19][CH2:18][CH:17]([C:20]3[NH:24][C:23]4[C:25]([C:29]([F:30])([F:31])[F:32])=[CH:26][CH:27]=[CH:28][C:22]=4[N:21]=3)[C:16]2=[O:33])[C@H:11]([CH2:34][S:35]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)(=[O:36])=[O:37])[CH2:10]1)[CH3:48]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178511573HCID 178511573, compound

Product 1

HCID 178464122HCID 178464122, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 47 (25 mg, 44 μmol) in 1,2-dichloroethane (2.7 mL) was added acetaldehyde (28 μL, 492 μmol) and acetic acid (8 μL, 96 μmol). The resulting mixture was stirred for 20 min, then sodium triacetoxyborohydride (31 mg, 144 μmol) was added. After stirring for 2 h, the mixture was diluted with EtOAc and washed sequentially with saturated aqueous NaHCO3, water, and brine. The organic phase was dried over Na2SO4, filtered, and the solvent was removed in vacuo. The residue was purified by preparative TLC (90:10:1 CHCl3/MeOH/NH4OH). After concentrating the material in vacuo, the resulting oil was dissolved in CH3CN/H2O/TFA and lyophilized to provide the title compound (8.5 mg, 26%) as a white solid and mixture of diastereomers: ESI MS m/z 577 [C29H35F3N4O3S+H]+.

Workup

  1. stirringAfter stirring for 2 h
  2. washwashed sequentially with saturated aqueous NaHCO3, water, and brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by preparative TLC (90:10:1 CHCl3/MeOH/NH4OH)
  7. concentrationAfter concentrating the material in vacuo
  8. dissolutionthe resulting oil was dissolved in CH3CN/H2O/TFA
  9. customto provide

Sources & evidence

ORD record
ord-8467dbf0ae8144af8b8253cd4df269e6
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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