1,4-Dideoxy-1,4-iminothreitol → 3-Bromo-N-(4-(chlorodifluoromethoxy)phenyl)-4-((3 S,4S)-3,4-dihydroxypyrrolidin-1-yl)benzamide

HRID 924120Notes

Reaction equation

HRID 924120 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1F)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([Cl:18])([F:17])[F:16])=[CH:10][CH:9]=1)=[O:6].[NH:23]1[CH2:27][C@H:26]([OH:28])[C@@H:25]([OH:29])[CH2:24]1>>[Br:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[N:23]1[CH2:27][C@H:26]([OH:28])[C@@H:25]([OH:29])[CH2:24]1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([Cl:18])([F:17])[F:16])=[CH:10][CH:9]=1)=[O:6]

Participants

3

Reactant 2

HCID 1461981,4-Dideoxy-1,4-iminothreitolHCID 867026223-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-4-fluorobenzamide

Product 1

HCID 899064003-Bromo-N-(4-(chlorodifluoromethoxy)phenyl)-4-((3 S,4S)-3,4-dihydroxypyrrolidin-1-yl)benzamide

Procedure

The title compound was prepared in an analogous fashion to that described in Stage 243.1 (20 h at 90° C.+3 h at 105° C.) using 3-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-4-fluorobenzamide and (3S,4S)-pyrrolidine-3,4-diol to afford a white amorphous solid. UPLC-MS (Condition 3) tR=1.01 min, m/z=476.8 [M+H]+.

Workup

  1. customthat described in Stage 243.1 (20 h at 90° C.+3 h at 105° C.)
  2. customto afford a white amorphous solid

Sources & evidence

ORD record
ord-6c4822148284425594fe9b49bb7297ab
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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