Formaldehyde → N-(N-Acetyl-tyrosinyl-valinyl-(4-benzyloxyprolinyl))-3-amino-4-oxobutanoic Acid

HRID 1292060Notes

Reaction equation

HRID 1292060 reaction equation
C(OC(=NNC(N)=O)C[CH:8]([NH:11][C:12](=[O:48])[C@@H:13]1[CH2:17][CH:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][N:14]1[C:26](=[O:47])[C@H:27]([CH:44]([CH3:46])[CH3:45])[NH:28][C:29](=[O:43])[C@H:30]([CH2:35][C:36]1[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=1)[NH:31][C:32](=[O:34])[CH3:33])[CH:9]=[O:10])(C)(C)C.F[C:55](F)(F)[C:56]([OH:58])=[O:57].CO.C=O>ClCCl.C(O)(=O)C>[C:32]([NH:31][C@H:30]([C:29]([NH:28][C@H:27]([C:26]([N:14]1[CH2:15][CH:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:17][C@H:13]1[C:12]([NH:11][CH:8]([CH:9]=[O:10])[CH2:55][C:56]([OH:58])=[O:57])=[O:48])=[O:47])[CH:44]([CH3:45])[CH3:46])=[O:43])[CH2:35][C:36]1[CH:37]=[CH:38][C:39]([OH:42])=[CH:40][CH:41]=1)(=[O:34])[CH3:33]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 6422Trifluoroacetic acidHCID 53915659N-(N-Acetyl-tyrosinyl-valinyl-(4-benzyloxyprolinyl))-3-amino-4-oxobutanoic acid tert-butyl ester semicarbazone

Product 1

HCID 22875500N-(N-Acetyl-tyrosinyl-valinyl-(4-benzyloxyprolinyl))-3-amino-4-oxobutanoic Acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

N-(N-Acetyl-tyrosinyl-valinyl-(4-benzyloxyprolinyl))-3-amino-4-oxobutanoic acid tert-butyl ester semicarbazone (270 mg) was dissolved into 10 ml of 25% trifluoroacetic acid in dichloromethane and stirred at room temperature for 3 hours. The mixture was concentrated to give a solid residue. The residue was dissolved into a 10 ml mixture of methanol:acetic acid:37% formaldehyde (3:1:1) and stirred at room temperature for 1 hour. The mixture was concentrated and the resulting residue purified by flash chromatography (SiO2) eluting with dichloromethane/methanol/formic acid (100:5:0.5) to give 37 mg of the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. customto give a solid residue
  3. concentrationThe mixture was concentrated
  4. customthe resulting residue purified by flash chromatography (SiO2)
  5. washeluting with dichloromethane/methanol/formic acid (100:5:0.5)

Sources & evidence

ORD record
ord-c6c36949eb3649b5a7087f0293d2938e
Source dataset
uspto-grants-1998_05
Patent number
US05756466

Reaction notes

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