Formic Acid → HCID 58765501, compound

HRID 859921Notes

Reaction equation

HRID 859921 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[OH:11][NH:12][CH:13]([CH2:38][C@@H:39]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH3:40])[CH2:14][S:15]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]#[C:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:26][CH:25]=2)[CH2:20][CH2:19]1)(=[O:17])=[O:16]>C(Cl)Cl>[OH:11][N:12]([CH:13]([CH2:14][S:15]([N:18]1[CH2:19][CH2:20][N:21]([C:24]2[CH:25]=[CH:26][C:27]([C:30]#[C:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:28][CH:29]=2)[CH2:22][CH2:23]1)(=[O:16])=[O:17])[CH2:38][C@@H:39]([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[CH3:40])[CH:1]=[O:3]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 86594845HCID 86594845, compound

Product 1

HCID 58765501HCID 58765501, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To formic acid (2.5 mL, 65 mmol) at 0° C. was added acetic anhydride (500 μL, 5.2 mmol) and the mixture was stirred at 0° C. for 10 minutes. This was added to a solution of 1-{[(4S)-2-(hydroxyamino)-4-phenylpentyl]sulfonyl}-4-[4-(phenylethynyl)phenyl]piperazine (345 mg, 0.685 mmol) in CH2Cl2 (5 mL) cooled to 0° C. The reaction was brought to RT and stirred for one hour. Volatiles were then removed in vacuo. The residue was then precipitated in MeOH (10 mL) and heated to 40° C. for two hours, dissolving. The solution was then cooled to RT and concentrated in vacuo. The residue was then purified by flash chromatography (silica gel, 1–2% MeOH in CH2Cl2) to give the title compound as a white foam (330 mg, 0.621 mmol, 91%).

Workup

  1. temperaturecooled to 0° C
  2. customwas brought to RT
  3. stirringstirred for one hour
  4. customVolatiles were then removed in vacuo
  5. customThe residue was then precipitated in MeOH (10 mL)
  6. temperatureheated to 40° C. for two hours
  7. dissolutiondissolving
  8. temperatureThe solution was then cooled to RT
  9. concentrationconcentrated in vacuo
  10. customThe residue was then purified by flash chromatography (silica gel, 1–2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-4bf865d330e0479c9c6f6cff71694fb4
Source dataset
uspto-grants-2006_12
Patent number
US07153857B2

Reaction notes

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