Methanol → H-Orn(Z)-ome hcl

HRID 1375746Notes

Reaction equation

HRID 1375746 reaction equation
[NH2:1][C@H:2]([C:17]([OH:19])=[O:18])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].S(Cl)([Cl:22])=O.[CH3:24]O>>[NH2:1][C@H:2]([C:17]([O:19][CH3:24])=[O:18])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[ClH:22]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 7009570H-Orn(Z)-OH

Product 1

HCID 13967650H-Orn(Z)-ome hcl

Procedure

To a solution of H-Orn(Z)—OH (1.00 μg, 3.76 mmol) in anhydrous MeOH (25 mL) at 0° C. was slowly added thionyl chloride (1.37 mL, 2.24 g, 18.8 mmol) as to maintain the internal reaction temperature below 10° C. After the addition was complete, the cold bath was removed, and stirring was continued for at rt 18 hours. The reaction was then concentrated under reduced pressure to afford a yellowish solid. Recrystallization with MeOH:EtOAc (1:6) afforded the desired product xliv as a white solid (600 mg, 0.190 mmol). The filtrate and EtOAc washings were cooled for 48 h at −20° C. to provide additional product xliv (177 mg, 0.56 1 mmol). The two batches (total: 777 mg, 2.46 mmol, 65%) were combined for further use.

Workup

  1. customat 0° C.
  2. temperatureto maintain the internal reaction temperature below 10° C
  3. additionAfter the addition
  4. customthe cold bath was removed
  5. customwas continued for at rt 18 hours
  6. concentrationThe reaction was then concentrated under reduced pressure
  7. customto afford a yellowish solid
  8. customRecrystallization with MeOH:EtOAc (1:6)

Sources & evidence

ORD record
ord-ec20b151455644cfb021c4cc010705f1
Source dataset
uspto-grants-2007_01
Patent number
US07169814B2

Reaction notes

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