Thionyl Chloride → HCID 10942556, compound

HRID 2166076Notes

Reaction equation

HRID 2166076 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@@H:6]([C:9]([OH:11])=O)[CH2:7][OH:8])=[O:4].S(Cl)(Cl)=O>CO>[OH:8][CH2:7][C@H:6]1[NH:5][C:3](=[O:4])[CH2:2][NH:1][C:9]1=[O:11]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1766440HCID 1766440, compound

Product 1

HCID 10942556HCID 10942556, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of glycyl-D-serine I (4 g) in methanol (12 ml) was treated with thionyl chloride (4 ml) dropwise over a 15 min period maintaining the temperature below 30°. The mixture was heated at 40°-50° for 3 h, and the solvent was evaporated in vacuo. The residue was triturated under diethyl ether and then dissolved in methanol (80 ml). Aqueous ammonia (8 ml) was added and the resulting solid was filtered off, to give the title compound as a solid (1.95 g) m.p. 218°.

Workup

  1. temperaturemaintaining the temperature below 30°
  2. temperatureThe mixture was heated at 40°-50° for 3 h
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was triturated under diethyl ether
  5. dissolutiondissolved in methanol (80 ml)
  6. additionAqueous ammonia (8 ml) was added
  7. filtrationthe resulting solid was filtered off

Sources & evidence

ORD record
ord-ccc4ece3ddd34dc1a243ccbe0bc188b3
Source dataset
uspto-grants-1990_07
Patent number
US04943578

Reaction notes

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