ethyl 1-[5-(4-iodo-1-methyl-1H-pyrazol-5-yl)-2H-tetrazol-2-yl]ethyl carbonate → (S)-ethyl 1-[5-(4-iodo-1-methyl-1H-pyrazol-5-yl)-2H-tetrazol-2-yl]ethyl carbonate

HRID 588381Notes

Reaction equation

HRID 588381 reaction equation
[C:1](=[O:20])([O:5][CH:6]([N:8]1[N:12]=[N:11][C:10]([C:13]2[N:17]([CH3:18])[N:16]=[CH:15][C:14]=2[I:19])=[N:9]1)[CH3:7])[O:2][CH2:3][CH3:4].C(=O)(O[C@@H](N1N=NC(C2N(C)N=CC=2I)=N1)C)OCC>>[C:1](=[O:20])([O:5][C@H:6]([N:8]1[N:12]=[N:11][C:10]([C:13]2[N:17]([CH3:18])[N:16]=[CH:15][C:14]=2[I:19])=[N:9]1)[CH3:7])[O:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 117652932ethyl 1-[5-(4-iodo-1-methyl-1H-pyrazol-5-yl)-2H-tetrazol-2-yl]ethyl carbonateHCID 117661191(R)-ethyl 1-[5-(4-iodo-1-methyl-1H-pyrazol-5-yl)-2H-tetrazol-2-yl]ethyl carbonate

Product 1

HCID 117661195(S)-ethyl 1-[5-(4-iodo-1-methyl-1H-pyrazol-5-yl)-2H-tetrazol-2-yl]ethyl carbonateYield 99.22%

Procedure

407.5 g of Preparation 23, ethyl 1-[5-(4-iodo-1-methyl-1H-pyrazol-5-yl)-2H-tetrazol-2-yl]ethyl carbonate was processed according to Chiral Preparative Chromatography Method 3, followed by concentration of each enantiomer to dryness in vacuo to give isomer 23a (177.4 g, 99.22%, 99.79% e.e.; tR=2.12 min) and isomer 23b (177.74 g, 98.83%, 98.46% e.e; tR=2.59 min).

Sources & evidence

ORD record
ord-de620e68b39745d5be629dc23662684a
Source dataset
uspto-grants-2016_01
Patent number
US09227956B2

Reaction notes

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