Methanol → HCID 57947411, compound

HRID 416397Notes

Reaction equation

HRID 416397 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([NH:12][C:13](=[O:36])[O:14][CH2:15][C@@H:16]([N:22]([CH3:35])[C:23]([NH:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:28]=1[Cl:34])=[O:24])[CH2:17][CH:18]([OH:21])[CH2:19][OH:20])=[CH:5]2.CO>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([NH:12][C:13](=[O:36])[O:14][CH2:15][C@@H:16]([N:22]([CH3:35])[C:23]([NH:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:28]=1[Cl:34])=[O:24])[CH2:17][C@H:18]([OH:21])[CH2:19][OH:20])=[CH:5]2

Participants

4

Reactant 2

HCID 887MethanolHCID 57947524HCID 57947524, compound

Product 1

HCID 57947411HCID 57947411, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of crude (2S)-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-4,5-dihydroxypentyl 6-fluoroisoquinolin-3-ylcarbamate (0.07 g) in DCM (1 mL) was loaded onto a TLC Silica gel 60 F254 (20×20 cm) plate and developed with a mixture of DCM and methanol (20:1). The top layer was collected and stirred in methanol (50 mL) for 10 min. After filtration, the filtrate was concentrated to give (2S,4S)-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-4,5-dihydroxypentyl 6-fluoroisoquinolin-3-ylcarbamate (0.01 g, 14.3%). LRMS (M+H+) m/z 523.2. The same process was applied to the bottom layer to give (2S,4R)-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-4,5-dihydroxypentyl 6-fluoroisoquinolin-3-ylcarbamate (27 mg, 38.6%). LRMS (M+H+) m/z 523.2.

Workup

  1. customThe top layer was collected
  2. filtrationAfter filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0bc98665984b414da50265dc7d606d00
Source dataset
uspto-grants-2012_01
Patent number
US08088793B2

Reaction notes

Loading…