Thionyl Chloride → (S)-Methyl 2-aminobut-3-enoate hydrochloride

HRID 58390Notes

Reaction equation

HRID 58390 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C@@H:4]([NH:7]C(OCC1C=CC=CC=1)=O)[CH:5]=[CH2:6].S(Cl)([Cl:21])=O>CO>[ClH:21].[CH3:1][O:2][C:3](=[O:18])[C@@H:4]([NH2:7])[CH:5]=[CH2:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10922916Z-L-a-vinyl-Gly-OMe

Product 1

HCID 86650247(S)-Methyl 2-aminobut-3-enoate hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Carboxylic acid 62 (0.350 g, 2.56 mmol) was suspended in methanol (10 mL). This was cooled in ice and 20% (v/v) thionyl chloride was added portionwise. The solution was stirred in ice for 1 h and then at rt for 18 h before being concentrated in vacuo to afford a white solid, 0.388 g, (100%).

Workup

  1. temperatureThis was cooled in ice
  2. concentrationat rt for 18 h before being concentrated in vacuo
  3. customto afford a white solid, 0.388 g, (100%)

Sources & evidence

ORD record
ord-0d6d36e2bcde44e7bacf077b0f5c66b6
Source dataset
uspto-grants-2016_09
Patent number
US09434762B2

Reaction notes

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