Carbon dioxide methanol → (S)-Benzyl(3,4-dihydroxybutyl)carbamate

HRID 525782Notes

Reaction equation

HRID 525782 reaction equation
C(=O)=O.CO.[OH:6][CH:7]([CH2:21][OH:22])[CH2:8][CH2:9][NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:13]([O:12][C:11](=[O:20])[NH:10][CH2:9][CH2:8][C@H:7]([OH:6])[CH2:21][OH:22])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 21973728Carbon dioxide methanolHCID 66736526benzyl N-(3,4-dihydroxybutyl)carbamate

Product 1

HCID 66782998(S)-Benzyl(3,4-dihydroxybutyl)carbamate

Procedure

The title compound was prepared by chiral separation (Preparative chiral SFC, ChiralPak® AD-H, 250×50 mm, mobile phase: CO2/MeOH (3:2), flow rate: 110 mL/min, back pressure: 100 bar, column temperature: 38° C., wavelength: 210 nm, cycletime: ˜4.0 min) of a racemic mixture of benzyl (3,4-dihydroxybutyl)carbamate (Prepared accordingly to WO2011107608), faster eluting isomer (Peak 1). Analytical chiral SFC (ChiralPak AD-3, 150×4.6 mm, eluent: CO2/MeOH+0.05% DEA (75:35), flow rate: 2.5 mL/min, back pressure: 100 bar, temperature: 35° C., 210 nm): tR=2.22 min.

Workup

  1. customPrepared accordingly to WO2011107608),
  2. washfaster eluting isomer (Peak 1)
  3. custom35° C., 210 nm

Sources & evidence

ORD record
ord-89b8effbf77b484bb2ebae113503ab9d
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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