Acetic Acid → HCID 178457503, compound

HRID 351386Notes

Reaction equation

HRID 351386 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.[CH3:44][C:45]([CH3:47])=O.C(O)(=O)C.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].[CH:45]([NH: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: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)([CH3:47])[CH3:44]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 178511573HCID 178511573, compound

Product 1

HCID 178457503HCID 178457503, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 47 (67 mg, 0.13 mmol) in 1,2-dichloroethane (7.3 mL) was added acetone (0.38 mL, 5.2 mmol) and acetic acid (30 μL, 0.51 mmol). The resulting mixture was stirred for 20 min, then sodium triacetoxyborohydride (110 mg, 0.52 mmol) 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 resulting clear, glassy solid was dissolved in CH3CN/H2O/TFA and lyophilized to provide the title compound (5.1 mg, 6%) as a white solid and mixture of diastereomers: ESI MS m/z 563 [C28H33F3N4O3S+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. dissolutionThe resulting clear, glassy solid was dissolved in CH3CN/H2O/TFA
  7. customto provide

Sources & evidence

ORD record
ord-7f133d88f60044179e1174c7769f355b
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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