4-Formylbenzoic acid → 3-[cyclopropylmethyl-(4-formylbenzoyl)amino]propionic Acid

HRID 1633889Notes

Reaction equation

HRID 1633889 reaction equation
[CH:1]1([CH2:4][NH:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])[CH2:3][CH2:2]1.[CH:11]([C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1)=[O:12].F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1>CN(C=O)C.C(N(C(C)C)CC)(C)C>[CH:1]1([CH2:4][N:5]([C:17](=[O:18])[C:16]2[CH:20]=[CH:21][C:13]([CH:11]=[O:12])=[CH:14][CH:15]=2)[CH2:6][CH2:7][C:8]([OH:10])=[O:9])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 120884-Formylbenzoic acidHCID 2733179PyBroPHCID 22502000N-(cyclopropylmethyl)-3-aminopropionic Acid

Product 1

HCID 225023043-[cyclopropylmethyl-(4-formylbenzoyl)amino]propionic Acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
25 °C

Procedure

To the above resin bound N-(cyclopropylmethyl) 3-aminopropionic acid (50 mg) was added 200 μmol 4-formylbenzoic acid (30 mg) dissolved in a mixture of 430 μL DMF and 70 μL diisopropylethylamine followed by 200 μmol bromo-tris-pyrrolidinophosphonium hexafluorophosphate (PyBrOP, 93 mg) dissolved in 500 μL DMF. The mixture was shaken at 25° C. for 4 hours followed by filtration and washing of the resin with 3×1 mL DMF and 1 mL trimethylorthoformate.

Workup

  1. filtrationfollowed by filtration
  2. washwashing of the resin with 3×1 mL DMF and 1 mL trimethylorthoformate

Sources & evidence

ORD record
ord-413e8db2a1634959be03a5de3c657230
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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