Diisopropylethylamine → HCID 69948825, compound

HRID 2268597Notes

Reaction equation

HRID 2268597 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:44][O:45][C:46](=[O:53])[CH2:47][CH2:48][NH:49][CH:50]([CH3:52])[CH3:51]>CN(C=O)C>[CH3:44][O:45][C:46](=[O:53])[CH2:47][CH2:48][N:49]([C:5](=[O:7])[C:4]1[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=[C:2]([Cl:1])[CH:3]=1)[CH:50]([CH3:52])[CH3:51]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 12774812Methyl 3-[(propan-2-yl)amino]propanoateHCID 129093413-Chloro-5-methoxybenzoic acid

Product 1

HCID 69948825HCID 69948825, compoundYield 102.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-chloro-5-methoxy-benzoic acid (0.932 g), TBTU (3.21 g) and in DMF (10 ml) was added DIPEA (1.73 ml) followed by 3-isopropylamino propionic acid methyl ester (0.871 g) after 10 min. The reaction mixture was stirred at room temperature for 48 h and then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic phase was washed with further water and 2M aqueous sodium hydroxide, water and dried with brine and over sodium sulphate and concentrated under reduced pressure to give the title compound as a brown oil (1.6 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with further water and 2M aqueous sodium hydroxide, water
  4. dry with materialdried with brine and over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dc6c1c94c12141539f7f9e9ad0967479
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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