Acetic-formic anhydride → HCID 11588997, compound

HRID 1008774Notes

Reaction equation

HRID 1008774 reaction equation
[OH:1][NH:2][CH:3]([C:20]#[C:21][CH2:22][CH2:23][CH3:24])[CH2:4][S:5]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)(=[O:7])=[O:6].[CH:25](OC(=O)C)=[O:26]>C1COCC1>[OH:1][N:2]([CH:3]([CH2:4][S:5]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)(=[O:6])=[O:7])[C:20]#[C:21][CH2:22][CH2:23][CH3:24])[CH:25]=[O:26]

Participants

4

Reactant 2

HCID 75269Acetic-formic anhydrideHCID 11573905HCID 11573905, compound

Product 1

HCID 11588997HCID 11588997, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-{[2-(hydroxyamino)hept-3-yn-1-yl]sulfonyl}-4-pyridin-2-ylpiperazine (157 mg; 0.45 mmol) in THF (5 mL) was added a solution of acetyl formate (200 mg, prepared as described by Kolle et al., 1983, Helvetica Chimica Acta, 66(8), 2760-8) in THF (2 mL). The reaction mixture was stirred at rt for 5 h and concentrated under reduced pressure. Purification of the crude by flash chromatography on silica (EtOAc:c-Hex, gradient from 50:50 to 100:0) gave the title compound as a white foam (90 mg, 53% yield). HPLC, Rt: 3.04 min (purity: 97.9%). LC/MS, M+(ESI): 381.3, M−(ESI): 379.2. 1H NMR (DMSO-d6) δ: 8.39 (brs, 0.4H), 8.18 (m, 1H), 8.08 (brs, 0.6H), 7.48 (m, 1H), 6.66 (m, 2H), 5.53 (brs, 0.4H), 5.01 (brs, 0.6H), 3.63 (m, 5H), 3.36 (m, 6H), 2.14 (m, 2H), 1.49 (sx, J=7.2 Hz, 2H), 0.93 (t, J=7.3 Hz, 3H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customPurification of the crude by flash chromatography on silica (EtOAc:c-Hex, gradient from 50:50 to 100:0)

Sources & evidence

ORD record
ord-e9313fe2abb74cba85837fd2db0b10a4
Source dataset
uspto-grants-2011_07
Patent number
US07973039B2

Reaction notes

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