HCID 72370696, compound → HCID 59735261, compound

HRID 525779Notes

Reaction equation

HRID 525779 reaction equation
C(=O)=O.CC(O)C.[OH:8][CH:9]([CH2:22][CH2:23][OH:24])[CH2:10][NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([O:13][C:12](=[O:21])[NH:11][CH2:10][C@@H:9]([OH:8])[CH2:22][CH2:23][OH:24])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 72370696HCID 72370696, compoundHCID 86586944Isopropanol carbon dioxide

Product 1

HCID 59735261HCID 59735261, compound

Procedure

The title compound was prepared by chiral separation (Preparative chiral SFC, ChiralPak® IC-H, 250×30 mm, mobile phase: CO2/iPrOH (75:35), flow rate: 60 mL/min, back pressure: 100 bar, column temperature: 38° C., wavelength: 210 nm, cycle time: ˜3.0 min) of a racemic mixture of benzyl (2,4-dihydroxybutyl)carbamate (Stage 97.2), slower eluting isomer (Peak 2). Analytical chiral SFC (ChiralCel® OD-3, 150×4.6 mm, eluent: CO2/iPrOH+0.05% DEA (8:2), flow rate: 2.4 mL/min, back pressure: 100 bar, temperature: 33° C., 210 nm): tR=3.77 min.

Workup

  1. washslower eluting isomer (Peak 2)
  2. custom33° C., 210 nm

Sources & evidence

ORD record
ord-5f5b23e14ee64fd4a6986f79c9320944
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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