Acetic Acid → HCID 15850491, compound

HRID 2297041Notes

Reaction equation

HRID 2297041 reaction equation
C([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]=1[C:17]([NH:19][C@H:20]([C:22]([NH:24][C@H:25]([CH:30]=[O:31])CC(O)=O)=[O:23])[CH3:21])=[O:18])C1C=CC=CC=1.C=O.[C:34]([OH:37])(=[O:36])[CH3:35]>CO>[CH2:8]([N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[C:9]1[C:17]([NH:19][C@H:20]([C:22]([NH:24][C@H:25]([CH:30]=[O:31])[CH2:35][C:34]([OH:37])=[O:36])=[O:23])[CH3:21])=[O:18])[C:16]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 712FormaldehydeHCID 86758628HCID 86758628, compound

Product 1

HCID 15850491HCID 15850491, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3S)-3-[( -Benzylindole-2-carbonyl)alaninyl] amino-4-oxobutanoic acid, semicarbazone (176 mg, 0.37 mmol) was dissolved in methanol (4.5 mL), formaldehyde (1.5 mL, 37% wt. aq) and acetic acid (1.5 mL) and the resulting mixture was stirred for 4 hours under a nitrogen atmosphere at room temperature. The reaction mixture was concentrated in vacuo, diluted with water, and extracted twice with ethyl acetate. The ethyl acetate solution was washed with brine, dried over sodium sulfate, and concentrated to give a crude product which was triturated with ether to afford the title product as a light green powder (113 mg, 72%). TLC: (methylene chloride:methanol:acetic acid, 20:1:1, silica gel): Rf=0.38; MS for C23H23N3O5; M+H+=422; M−H+420. 1H-NMR (CD3OD): δ7.65 (d, J=8.0, 1H), 7.37 (dd, J=8.2, 0.8, 1H), 7.24-7.04 (m, 8H), 5.87-5.73 (m, 2H) 4.60-4.49 (m, 2H), 4.32-4.23 (m, 1H), 2.69-2.44 (m, 2H), 1.41 (d, J=7.1, 2 sets, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted twice with ethyl acetate
  4. washThe ethyl acetate solution was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto give a crude product which
  8. customwas triturated with ether

Sources & evidence

ORD record
ord-89650168d67648e7a984d0bb1eb96c2e
Source dataset
uspto-grants-2002_12
Patent number
US06489353B2

Reaction notes

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