1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-2-(4-methylbenzenesulfonamido)pent-4-ynamide

HRID 2219881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2219881
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([CH2:16][C:17]#[CH:18])[C:13](O)=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C1C=[N:23]C2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH4+].[Cl-].CCN=C=NCCCN(C)C>CN(C=O)C.O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([CH2:16][C:17]#[CH:18])[C:13]([NH2:23])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 10978432(R)-2-(4-methylbenzenesulfonamido)pent-4-ynoic acid

Produkt 1

HCID 86604882(R)-2-(4-methylbenzenesulfonamido)pent-4-ynamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of (R)-2-(4-methylphenyl sulfonamido)pent-4-ynoic acid (1.0 g, 3.7 mmol), HOAt (0.76 g, 5.6 mmol), iPr2NEt (2.17 g, 16.9 mmol), NH4Cl (0.6 g, 11 mmol), and EDCI (1.07 g, 5.61 mmol) in 20 mL DMF was stirred for 18 h at RT. Water was added, which caused a precipitate to form. The white solid was filtered and air dried to afford the title compound. MS (m/z, m+1): 267.3.

Aufarbeitung

  1. customto form
  2. filtrationThe white solid was filtered
  3. customair dried

Quellen und Nachweise

ORD-Eintrag
ord-1dd3279a79fe422c93fd7891c6e3bdaf
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07414134B2

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