(3R,4R,7S)-4-azido-7-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-3-ol → tert-butyl N-[(3R,4R,7S)-3-methoxy-7-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-4-yl]carbamate

HRID 521885Notes

Reaction equation

HRID 521885 reaction equation
[CH3:1][O:2][CH:3]1[CH:9]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:8][CH2:7][CH:6]([C:18]2[N:19]([CH3:26])[N:20]=[CH:21][C:22]=2[N+:23]([O-:25])=[O:24])[O:5][CH2:4]1.N([C@@H]1CC[C@@H](C2N(C)N=CC=2[N+]([O-])=O)OC[C@@H]1O)=[N+]=[N-]>>[CH3:1][O:2][C@@H:3]1[C@H:9]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:14])[CH3:15])[CH2:8][CH2:7][C@@H:6]([C:18]2[N:19]([CH3:26])[N:20]=[CH:21][C:22]=2[N+:23]([O-:25])=[O:24])[O:5][CH2:4]1

Participants

3

Reactant 2

HCID 86713835(3R,4R,7S)-4-azido-7-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-3-olHCID 86713837tert-Butyl N-[3-methoxy-7-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-4-yl]carbamate

Product 1

HCID 86713836tert-butyl N-[(3R,4R,7S)-3-methoxy-7-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-4-yl]carbamate

Procedure

Following the procedure for Intermediate 58 starting from (3R,4R,7S)-4-azido-7-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-3-ol gave tert-butyl N-[(3R,4R,7S)-3-methoxy-7-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-4-yl]carbamate as a colourless oil (357 mg, 32% over three steps). 1H NMR (400 MHz, CDCl3) δ 8.00 (s, 1H), 5.60-5.53 (m, 1H), 5.12-5.02 (m, 1H), 4.21-4.08 (m, 2H), 4.01 (s, 3H), 3.79 (dd, J=13.2, 4.4 Hz, 1H), 3.75-3.70 (m, 1H), 3.41 (s, 3H), 2.28-2.07 (m, 1H), 1.97-1.89 (m, 2H), 1.80-1.72 (m, 1H), 1.47 (s, 9H).

Sources & evidence

ORD record
ord-b45698ceca6b43d1aac35f552cdaca9a
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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