Sodium Hydroxide → HCID 178444544, Verbindung

HRID 1450736

Reaktionsgleichung

Reaktionsgleichung von HRID 1450736
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([OH:14])=O)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C(Cl)(=O)C(Cl)=O.[NH2:21][C@@H:22]([C:26]([OH:28])=[O:27])[C@@H:23]([CH3:25])[OH:24].[OH-].[Na+]>C1(C)C=CC=CC=1.C(#N)C.C1COCC1>[CH2:1]([C@H:6]1[CH2:7][CH2:8][C@H:9]([C:12]([NH:21][C@@H:22]([C:26]([OH:28])=[O:27])[C@@H:23]([CH3:25])[OH:24])=[O:14])[CH2:10][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Komponenten

8

Edukt 4

HCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 90624D-AllothreonineHCID 178444557HCID 178444557, Verbindung

Produkt 1

HCID 178444544HCID 178444544, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of trans-4-pentylcyclohexane carboxylic acid (198 mg, 1.0 mmol) in dry toluene (1 mL) is treated with oxalyl chloride (760 mg, 5.9 mmol) at 0° C. and the mixture is stirred for 2 h at the same temperature and 1 h at room temperature. Excess reagent is removed in vacuo. A solution of the crude acid chloride in dry acetonitrile (2 mL) is added to a mixture of D-allo-Thr (100 mg, 0.85 mmol), 2N aq. NaOH (600 μl, 1.20 meq) and TEA (85 mg, 0.85 mmol) in THF (1.5 mL), following the procedure described in Example 1. The crude product 2c-6 is purified by chromatography (1.5×18 cm column, 5% CH3OH and 0.4% HOAc in CH2Cl2): NMR δ0.88 (t, j≈7, 3H), 4.15 (m, 1H), 4.54 (m, 1H), 6.49 (d, 1H); MS (CI, CH4) m/z 300 (M+H).

Aufarbeitung

  1. customExcess reagent is removed in vacuo
  2. customis purified by chromatography (1.5×18 cm column, 5% CH3OH and 0.4% HOAc in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-1a57e3cdf7ba4b32b53f675e838cfe23
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05602275

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