Ethyl Acetate → (S)-4-(2-(4-aminobenzylcarbamoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide

HRID 1776463Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N+:4]([O-:40])[CH:5]=[C:6]([Cl:39])[C:7]=1[CH2:8][C@@H:9]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH:31]([F:33])[F:32])=[C:26]([O:34][CH2:35][CH:36]2[CH2:38][CH2:37]2)[CH:25]=1)[O:10][C:11](=[O:23])[NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1.CCOC(C)=O>C1COCC1.C([O-])(O)=O.[Na+]>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][NH:12][C:11]([O:10][C@H:9]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH:31]([F:32])[F:33])=[C:26]([O:34][CH2:35][CH:36]3[CH2:38][CH2:37]3)[CH:25]=2)[CH2:8][C:7]2[C:2]([Cl:1])=[CH:3][N+:4]([O-:40])=[CH:5][C:6]=2[Cl:39])=[O:23])=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(4-nitrobenzylcarbamoyloxy)ethyl)pyridine 1-oxide (200 mg, 0.334 mmol) in THF (10 ml), SnCl2 dihydrate (603 mg, 2.67 mmol) was added, and the mixture was stirred at 60° C. for 5 hours, then the mixture was diluted with NaHCO3 sat (pH=7) followed by the addition of EtOAc and filtered trough a celite pad. The inorganic phase was extracted with EtOAc. The combined organic layers were rinsed with brine, dried over Na2SO4 and evaporated affording the desired product (190 mg, 0.334 mmol, 100% yield, MS/ESI+ 568.3 [MH]+).

Workup

filtrationfiltered trough a celite pad
extractionThe inorganic phase was extracted with EtOAc
washThe combined organic layers were rinsed with brine
dry with materialdried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-2e9a96e59e0e48c6a71cebfc6b589085
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265768B2

Reaction notes

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