Sodium Hydroxide → HCID 178444544, Verbindung

HRID 1033779

Reaktionsgleichung

Reaktionsgleichung von HRID 1033779
[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% CH30H and 0.4% HOAc in CH2Cl2): NMR δ0.88 (t, J≃7, 3H), 4.15 (m, 1 H), 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% CH30H and 0.4% HOAc in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-d8c3035e93d045239f92b7cb1929a63a
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05312831

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