Methanol → AG-H-13503

HRID 58394Notes

Reaction equation

HRID 58394 reaction equation
[NH2:1][C@@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][OH:10])[C:3]([OH:5])=[O:4].O=S(Cl)Cl.[CH3:15]O>>[CH3:15][O:4][C:3](=[O:5])[C@@H:2]([NH2:1])[CH2:6][CH2:7][CH2:8][CH2:9][OH:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 97725epsilon-Hydroxynorleucine

Product 1

HCID 11680006AG-H-13503Yield 99%

Conditions

Temperature
0 °C

Procedure

(S)-2-Amino-6-hydroxy-hexanoic acid (Chemstep) (5.54 mmol, 1.37 g) was dissolved in 100 mL of MeOH and cooled at 0° C. SOCl2 (13.8 mmol, 1 mL, 2.5 eq) was added dropwise. The reaction mixture was stirred overnight at room temperature after which time the solvent was removed in vacuo. The crude solid was recrystallised from MeOH (3×100) to give the methyl ester 82 as an oil (5.52 mmol, 0.89 g, 99%).

Workup

  1. customwas removed in vacuo
  2. customThe crude solid was recrystallised from MeOH (3×100)

Sources & evidence

ORD record
ord-3cbcc4ccb6774212b76d104c1944ad47
Source dataset
uspto-grants-2016_09
Patent number
US09434762B2

Reaction notes

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