4-Aminophenylacetic acid → HCID 57977868, compound

HRID 1865855Notes

Reaction equation

HRID 1865855 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]([OH:18])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:52][C:53]1[CH:58]=[CH:57][C:56]([CH2:59][C:60]([OH:62])=[O:61])=[CH:55][CH:54]=1>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:18])[NH:52][C:53]1[CH:54]=[CH:55][C:56]([CH2:59][C:60]([OH:62])=[O:61])=[CH:57][CH:58]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 145334-Aminophenylacetic acidHCID 81531DiisopropylethylamineHCID 101987Benzyloxycarbonyl-L-prolineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 57977868HCID 57977868, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (S)-Pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (F.W.=249.27, 1.5 g, 4.0 mmol), HATU (1.6 g, 3.9 mmol), and DIEA (0.7 mL, 4.97 mmol) in DMF (30 mL) was stirred at room temperature for 1 h. (4-Amino-phenyl)-acetic acid (FW=151.17, 0.5 g, 3.31 mmol) was added. The reaction mixture was stirred at room temperature for 20 h. The mixture was filtered and separated by reverse phase HPLC (0-100% of buffer B; buffer A: water containing 0.1% TFA; buffer B: MeCN containing 0.1% TFA). The combined fraction was evaporated to furnish the desired product (S)-2-(4-Carboxymethyl-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester.

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. customseparated by reverse phase HPLC (0-100% of buffer B
  4. customThe combined fraction was evaporated

Sources & evidence

ORD record
ord-fad0494c2d814173863189f75f4f8e4a
Source dataset
uspto-grants-2009_12
Patent number
US07629340B2

Reaction notes

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