Hydrochloric Acid → HCID 55288372, compound

HRID 1926563Notes

Reaction equation

HRID 1926563 reaction equation
[OH:1][CH:2]1[CH:6]([CH2:7][S:8][CH3:9])[CH2:5][NH:4][CH2:3]1.CO.Cl>>[OH:1][C@H:2]1[C@H:6]([CH2:7][S:8][CH3:9])[CH2:5][NH:4][CH2:3]1

Participants

4

Procedure

N-Protected 3-hydroxy-4-(methylthiomethyl)-pyrrolidine (8.2 g, 33.2 mmol) was dissolved in methanol (40 mL, 33.2 mmol) and to this was added hydrochloric acid (10 mL, 326 mmol) and the resulting solution concentrated in vacuo. This step was repeated, whereupon TLC (10% v/v 7N NH3 in MeOH-dichloromethane) indicated complete deprotection. Column chromatography on silica eluted with 10-20% 7N NH3 in MeOH-dichloromethane afforded the title compound (4.3 g, 29.2 mmol, 88% yield).

Workup

  1. concentrationthe resulting solution concentrated in vacuo
  2. washColumn chromatography on silica eluted with 10-20% 7N NH3 in MeOH-dichloromethane

Sources & evidence

ORD record
ord-09b2ece7492541ffa9265b2924c6dacd
Source dataset
uspto-grants-2012_05
Patent number
US08183019B2

Reaction notes

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