Acetic Acid → HCID 21253300, compound

HRID 1530938Notes

Reaction equation

HRID 1530938 reaction equation
Cl.[C:2]1([CH:8]([SH:14])[CH:9]([C:11]([OH:13])=[O:12])[NH2:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15](O)(=O)C>C=O>[C:2]1([CH:8]2[S:14][CH2:15][NH:10][CH:9]2[C:11]([OH:13])=[O:12])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 13854699HCID 13854699, compound

Product 1

HCID 21253300HCID 21253300, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Procedure

A mixture of β-phenyl-DL-cysteine hydrochloride [HT Nagasawa et al, J. Med. Chem (1987) 30, 1373] (1.32 g, 5.65 mmol) in acetic acid (11 ml) and formaldehyde (37 wt % aqueous solution, 0.43 ml) was heated to 80° to give a cloudy solution that was cooled to 30° and stirred for 2.5 h, then stood at room temperature for 16 h. The white precipitate was collected by filtration, washed with Et2O and dried in vacuo to give the title compound (1.04 g, 88%). δH (DMSO-d6) 7.57-7.54 (2 H, m, Ar—H), 7.40-7.29 (3 H, m, Ar—H), 4.90 (1 H, d, CHα-Thiopro), 4.59 (2 H, d, J 9.3 Hz, NCH2S), 4.46 (1 H, d, J 9.8 Hz, CHPh). m/z (ESI, 60 V) 210 (MH+).

Workup

  1. temperaturewas heated to 80°
  2. customto give a cloudy solution that
  3. temperaturewas cooled to 30°
  4. waitstood at room temperature for 16 h
  5. filtrationThe white precipitate was collected by filtration
  6. washwashed with Et2O
  7. customdried in vacuo

Sources & evidence

ORD record
ord-28bac35873524ef0909c68f3d99be6b4
Source dataset
uspto-grants-2001_03
Patent number
US06197794B1

Reaction notes

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