Formic Acid → HCID 11588105, compound

HRID 1008773Notes

Reaction equation

HRID 1008773 reaction equation
C(O[C:5](=[O:7])C)(=O)C.C(O)=O.[OH:11][NH:12][CH:13]([C:30]#[CH:31])[CH2:14][S:15]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[CH2:20][CH2:19]1)(=[O:17])=[O:16]>C1COCC1>[OH:11][N:12]([CH:13]([CH2:14][S:15]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[CH2:20][CH2:19]1)(=[O:16])=[O:17])[C:30]#[CH:31])[CH:5]=[O:7]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 11565825HCID 11565825, compound

Product 1

HCID 11588105HCID 11588105, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetic anhydride (25 mg; 0.24 mmol; 5.0 eq.) was added to cold (0° C.) formic acid (111 mg; 2.42 mmol; 50.0 eq.). The mixture was stirred 1 h, then a 1 M solution of 1-{[2-(hydroxyamino)-3-butynyl]sulfonyl}-4-(2-pyridinyl)piperazine (15 mg; 0.05 mmol; 1.0 eq.) in THF was added. After 4 h, the solvents were evaporated and the crude product was purified on silicagel (80/20 EtOAc/c-Hex) to give the title compound (12) as a colorless oil (2.3 mg, 14% yield). LC/MS, M+(ESI): 339.2, M−(ESI): 337.1.

Workup

  1. waitAfter 4 h
  2. customthe solvents were evaporated
  3. customthe crude product was purified on silicagel (80/20 EtOAc/c-Hex)

Sources & evidence

ORD record
ord-bc31702e8583421abfbb61806fa12ca7
Source dataset
uspto-grants-2011_07
Patent number
US07973039B2

Reaction notes

Loading…