HCID 86713814, compound → (3R,4R,7S)-4-azido-7-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-3-ol

HRID 521884Notes

Reaction equation

HRID 521884 reaction equation
[N:1]([CH:4]1[CH2:10][CH2:9][CH:8]([C:11]2[N:12]([CH3:19])[N:13]=[CH:14][C:15]=2[N+:16]([O-:18])=[O:17])[O:7][CH2:6][CH:5]1[OH:20])=[N+:2]=[N-:3].N([C@@H]1CC[C@@H](C2N(C)N=CC=2[N+]([O-])=O)OCC1=O)=[N+]=[N-]>>[N:1]([C@@H:4]1[CH2:10][CH2:9][C@@H:8]([C:11]2[N:12]([CH3:19])[N:13]=[CH:14][C:15]=2[N+:16]([O-:18])=[O:17])[O:7][CH2:6][C@@H:5]1[OH:20])=[N+:2]=[N-:3]

Participants

3

Reactant 2

HCID 86713814HCID 86713814, compoundHCID 86713834(4R,7S)-4-azido-7-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-3-one

Product 1

HCID 86713835(3R,4R,7S)-4-azido-7-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-3-olYield 74%

Procedure

Following the procedure for Intermediate 57 starting from (4R,7S)-4-azido-7-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-3-one gave (3R,4R,7S)-4-azido-7-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-3-ol as a dark orange oil (850 mg, 74%). 1H NMR (400 MHz, CDCl3) δ 8.02 (s, 1H), 5.68-5.60 (m, 1H), 4.24-4.14 (m, 3H), 4.01 (s, 3H), 3.72-3.58 (m, 1H), 2.45-2.31 (m, 1H), 2.30-2.09 (m, 2H), 2.01-1.81 (m, 2H).

Sources & evidence

ORD record
ord-31a4a22ce2194d49b5e19875e6553548
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

Loading…