Isoamyl Nitrite → 2-(R)-(4-Acetoxymethyl-1H-indazol-5-ylmethyl)-succinic acid diethyl ester

HRID 132330Notes

Reaction equation

[N:1](OCCC(C)C)=O.[CH2:9]([O:11][C:12](=[O:34])[C@H:13]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[C:23]([CH3:28])[C:22]=1[CH2:29][O:30][C:31](=[O:33])[CH3:32])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:10]>C(O)(=O)C.C(Cl)(Cl)Cl.ClCCl>[CH2:9]([O:11][C:12](=[O:34])[C@H:13]([CH2:20][C:21]1[C:22]([CH2:29][O:30][C:31](=[O:33])[CH3:32])=[C:23]2[C:24](=[CH:25][CH:26]=1)[NH:27][N:1]=[CH:28]2)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:10]

Participants

Conditions

Temperature: 0 °C

Procedure

Isoamyl nitrite (170 μL, 1.3 mmol) was added dropwise to a cooled (water ice bath) solution of 2-(R)-(2-acetoxymethyl-4-amino-3-methyl-benzyl)-succinic acid diethyl ester in 5% acetic acid—chloroform (5 mL). Mixture was stirred at 0° C. for 1.5 hours. Mixture was diluted with dichloromethane (20 mL) and then washed with saturated aqueous sodium bicarbonate (2×20 mL). Organic was dried (magnesium sulfate), filtered and concentrated in vacuo. Title compound was obtained as amber oil in 99% yield. MS m/e (M+H)+=377.1.

Workup

washwashed with saturated aqueous sodium bicarbonate (2×20 mL)
dry with materialOrganic was dried (magnesium sulfate)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-426b6057b1a14ed18eed88f9dbe1e6b8
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384931B2

Reaction notes

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