Acetic Acid → HCID 57654653, Verbindung

HRID 1175128Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1175128
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([CH2:12][OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31].C(O)(=O)C>C(Cl)Cl.O>[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([CH2:12][O:13][S:30]([CH3:29])(=[O:32])=[O:31])[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 576546571,1-Dimethylethyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-3-(hydroxymethyl)-1-azetidinecarboxylate

Produkt 1

HCID 57654653HCID 57654653, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

3-tert-Butoxycarbonylamino-3-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester (490 mg; 1.6 mmol) and triethylamine (1.7 ml; 19 mmol), dissolved in CH2Cl2 (3 ml), are cooled to −5° C. and treated with methanesulfonyl chloride (280 mg; 2.43 mmol). The reaction mixture is kept at 0° C. for 35 minutes, poured on 10% acetic acid in water and extracted with TBME. The combined organic phases are washed with 2N Na2CO3, dried over Na2SO4, filtered and evaporated to dryness, yielding the desired product as colorless crystals. 1H-NMR (400 MHz; DMSO-d6: 7.75 (bs, 1H); 4.40 (s, 2H); 3.81 (bs, 4H); 3.23 (s, 3H); 1.40 (s, 9H); 1.38 (s, 9H). MS (m/z) ES+: 381 (MH+).

Aufarbeitung

  1. extractionextracted with TBME
  2. washThe combined organic phases are washed with 2N Na2CO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-6434a0738b8845ea8228d4f9ffac7488
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07838674B2

Notizen zur Reaktion

Wird geladen…