Acetic-formic anhydride → HCID 11662613, compound

HRID 1008775Notes

Reaction equation

HRID 1008775 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH:18]([NH:29][OH:30])[C:19]#[C:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=3)(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH:31](OC(=O)C)=[O:32]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH:18]([N:29]([OH:30])[CH:31]=[O:32])[C:19]#[C:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=3)(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 75269Acetic-formic anhydrideHCID 11561100HCID 11561100, compound

Product 1

HCID 11662613HCID 11662613, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(4-fluorophenyl)-4-{[2-(hydroxyamino)-4-(3-methoxyphenyl)but-3-yn-1-yl]sulfonyl}piperazine (349 mg; 0.81 mmol) and acetyl formate (prepared as described by Koller et al., 1983, above 8; 0.58 mL of a 1.39 M solution in THF; 0.81 mmol) was stirred at rt for 1 h. THF was removed under reduced pressure and replaced by MeOH. The solution was heated at 60° C. for 1 h and concentrated under reduced pressure. Purification of the crude by flash chromatography on silica (EtOAc:c-Hex 60:40 to 100:0) gave the title compound as an orange oil (90 mg, 24% yield). HPLC, Rt: 3.69 min (purity: 99.3%). LC/MS, M+(ESI): 462.3. 1H NMR (DMSO-d6) δ: 8.45 (brs, 0.4H), 8.13 (brs, 0.6H), 7.19 (m, 1H), 6.97-7.04 (m, 7H), 5.80 (brs, 0.4H), 5.25 (brs, 0.6H), 3.77 (s, 3H), 3.68 (brs, 1H), 3.44 (m, 6H), 3.14 (m, 4H).

Workup

  1. customTHF was removed under reduced pressure
  2. temperatureThe solution was heated at 60° C. for 1 h
  3. concentrationconcentrated under reduced pressure
  4. customPurification of the crude by flash chromatography on silica (EtOAc:c-Hex 60:40 to 100:0)

Sources & evidence

ORD record
ord-b58e4066af2c407aaf56ea9a51fad96b
Source dataset
uspto-grants-2011_07
Patent number
US07973039B2

Reaction notes

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