Acetic Acid → HCID 15850490, compound

HRID 1531709Notes

Reaction equation

HRID 1531709 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-2380a60d503d4adaa14d351a13028fa8
Source dataset
uspto-grants-2001_03
Patent number
US06200969B1

Reaction notes

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