Water → HCID 18394418, compound

HRID 1602020Notes

Reaction equation

HRID 1602020 reaction equation
[NH2:1][C@H:2]([CH2:6][C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[C:3]([OH:5])=[O:4].[C:12](OC(=O)C)(=[O:14])C.O>C(O)=O>[CH:12]([NH:1][C@H:2]([CH2:6][C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[C:3]([OH:5])=[O:4])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 7111750D-2-Thienylalanine

Product 1

HCID 18394418HCID 18394418, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
0 °C

Procedure

(2R)-2-Amino-3-(2-thienyl)propionic acid (5.00 g, 29.2 mmol) was dissolved in formic acid (50 ml). The solution was cooled to 0° C. Acetic acid anhydride (20 ml) was added dropwise. The reaction mixture was stirred for 16 h, while it was warming up to room temperature. It was cooled to 0° C. Water (20 ml) was added dropwise. The solution was warmed to room temperature. The solvent was removed in vacuo. The residue was suspended in ethyl acetate (20 ml). The precipitation was filtered off, collected, and dried in vacuo, to give 3.60 g of crude (2R)-2-(formylamino)-3-(2-thienyl)propionic acid, which was used for the following step.

Workup

  1. temperaturewas warming up to room temperature
  2. temperatureIt was cooled to 0° C
  3. temperatureThe solution was warmed to room temperature
  4. customThe solvent was removed in vacuo
  5. customThe precipitation
  6. filtrationwas filtered off
  7. customcollected
  8. customdried in vacuo

Sources & evidence

ORD record
ord-6ddae97f9a9c4b6da03f1514795152bf
Source dataset
uspto-grants-1999_11
Patent number
US05977178

Reaction notes

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