p-Toluenesulfonic acid → HCID 86604865, compound

HRID 1432003Notes

Reaction equation

HRID 1432003 reaction equation
CO[CH:3](OC)[CH2:4][NH:5][C:6](=[O:21])[C@H:7]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH2:8][C:9]#[CH:10].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[C:15]1([S:12]([N:11]2[CH:3]=[CH:4][NH:5][C:6](=[O:21])[C@H:7]2[CH2:8][C:9]#[CH:10])(=[O:14])=[O:13])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86604861HCID 86604861, compound

Product 1

HCID 86604865HCID 86604865, compound

Conditions

Temperature
60 °C

Procedure

A mixture of (R)-N-(2,2-dimethoxyethyl)-2-(benzenesulfonamido)pent-4-ynamide (10.55 g, 30.99 mmol) and p-toluenesulfonic acid (1.47 g, 7.75 mmol) p-dioxane (100 mL) was heated to 60° C. for 36 h. The reaction mixture was cooled, concentrated and taken up in EtOAc. After the organic mixture had stirred, a precipitate had formed that was filtered to afford the product as a tan solid. 1H NMR (300 MHz, DMSO-d6): δ 2.98 (s, 1H), 3.35 (d, 7.0 Hz, 2H), 4.35 (t, 7.0 Hz, 1H), 5.98 (m, 2H), 7.71 (m, 5H), 9.65 (s, 1H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. customa precipitate had formed
  4. filtrationthat was filtered

Sources & evidence

ORD record
ord-430fb699208c49df9d771789f7348644
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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