Methanol → HCID 22591851, compound

HRID 749512Notes

Reaction equation

HRID 749512 reaction equation
[NH2:1][CH:2]([C:7]1[CH:16]=[CH:15][C:10]2[O:11][CH2:12][CH2:13][O:14][C:9]=2[CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:21]O>>[NH2:1][CH:2]([C:7]1[CH:16]=[CH:15][C:10]2[O:11][CH2:12][CH2:13][O:14][C:9]=2[CH:8]=1)[CH2:3][C:4]([O:6][CH3:21])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 35364503-amino-3-(2,3-dihydro-1,4-benzodioxin-6-yl)propanoic acid

Product 1

HCID 22591851HCID 22591851, compound

Procedure

3-Amino-3-(2,3-dihydro-1,4-benzodioxin-6-yl)propionic acid [synthesis according to instructions known from the literature (e.g., L. Lázár, T. Martinek, G. Bernáth, F. Fülöp, Synth. Comm. 1998, 28, 219-224)]is introduced into a vessel in methanol (about 0.5 to 1.0 mol/l) and admixed dropwise at 0° C. with 1.2 eq of thionyl chloride. When the addition has been made the reaction mixture is stirred at room temperature overnight and subsequently concentrated. The residue is dissolved in a little methanol and the product is precipitated with diethyl ether. The solid is filtered off with suction, washed repeatedly with diethyl ether and dried under reduced pressure.

Workup

  1. additionWhen the addition
  2. concentrationsubsequently concentrated
  3. dissolutionThe residue is dissolved in a little methanol
  4. customthe product is precipitated with diethyl ether
  5. filtrationThe solid is filtered off with suction
  6. washwashed repeatedly with diethyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-574582ea62f643f28a2b4325e5801890
Source dataset
uspto-grants-2008_07
Patent number
US07402683B2

Reaction notes

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