Acetic Acid → (5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-4,5-dihydro-1H-pyrazole-5-carboxylic acid

HRID 1396933Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1396933
[NH:1]1[CH:5]([C:6]([OH:8])=[O:7])[CH2:4][CH:3]=[N:2]1.[CH:9]1([CH2:14][C@H:15]([CH2:19][N:20]([CH:29]=[O:30])[O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:16](F)=[O:17])[CH2:13][CH2:12][CH2:11][CH2:10]1.CCN(C(C)C)C(C)C.CC(O)=O>C(Cl)Cl>[CH:9]1([CH2:14][C@H:15]([CH2:19][N:20]([CH:29]=[O:30])[O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:16]([N:1]2[C@H:5]([C:6]([OH:8])=[O:7])[CH2:4][CH:3]=[N:2]2)=[O:17])[CH2:13][CH2:12][CH2:11][CH2:10]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 128798564,5-dihydro-1H-pyrazole-5-carboxylic acidHCID 86706340(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl fluoride

Produkt 1

HCID 86706370(5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-4,5-dihydro-1H-pyrazole-5-carboxylic acidAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

4,5-Dihydro-1H-pyrazole-5-carboxylic acid (939 mg, 8.23 mmol) in 20 ml of DCM was added into a solution of (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl fluoride (3035 mg, 9.88 mmol) in 21.8 ml of DCM, and followed by Hunig's base (4.3 ml, 24.69 mmol). The resulting solution was stirred at ambient temperature for 1 hr. HOAc (8 ml) was added to neutralize the solution, and then it was purified by RP-HPLC to give (5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-4,5-dihydro-1H-pyrazole-5-carboxylic acid (660 mg, 1.644 mmol, 40% yield). MS (ES+) m/z 401.9 (MH+).

Aufarbeitung

  1. customit was purified by RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-159b892d968e4848a6292769e74f3dea
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901119B2

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