Acetic Acid → HCID 15850490, compound

HRID 1860482Notes

Reaction equation

HRID 1860482 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([N:13](C1C=CC=CC=1)[C@H:14]([C:16]([NH:18][C@H:19]([CH:24]=[O:25])[CH2:20][C:21]([OH:23])=[O:22])=[O:17])[CH3:15])=[O:12].C=O.[C:34](O)(=O)[CH3:35]>CO>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([NH:13][C@H:14]([C:16]([NH:18][C@H:19]([CH:24]=[O:25])[CH2:20][C:21]([OH:23])=[O:22])=[O:17])[CH2:15][C:35]1[CH:34]=[CH:5][CH:4]=[CH:3][CH:11]=1)=[O:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 712FormaldehydeHCID 57072570HCID 57072570, compound

Product 1

HCID 15850490HCID 15850490, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3S)-3-[(1-Methylindole-2-carbonyl)phenyl-alaninyl]amino-4-oxobutanoic acid, semicarbazone (116 mg, 0.25 mmol) were dissolved in methanol (3 mL), formaldehyde (1 mL, 37% wt. aq) and acetic acid (1 mL) and the resulting solution was stirred for 9 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 brown powder (26 mg, 25%). TLC: (methylene chloride:methanol:acetic acid, 20:1:1, silica gel): Rf=0.33; MS(EI) for C23H21N3O5; M+H+=422; M−H+=420.

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-012748cdae574ea980dea2967b5185c0
Source dataset
uspto-grants-2003_03
Patent number
US06531467B2

Reaction notes

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