Hydrochloric Acid → HCID 54025803, compound

HRID 1107990Notes

Reaction equation

HRID 1107990 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[C:5]([O:13][CH2:14][C:15]3[C:16]([Cl:33])=[C:17]([S:22]([N:25]4[CH2:32][CH2:31][CH2:30][C@H:26]4[C:27]([OH:29])=O)(=[O:24])=[O:23])[CH:18]=[CH:19][C:20]=3[Cl:21])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C1C=[N:38]C2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.NC[CH2:57][CH2:58][C:59]([O:61][CH3:62])=[O:60].Cl>CN(C)C=O.CN1CCOCC1.O.ClCCl>[CH3:62][O:61][C:59](=[O:60])[CH2:58][CH2:57][NH:38][C:27]([CH:26]1[CH2:30][CH2:31][CH2:32][N:25]1[S:22]([C:17]1[CH:18]=[CH:19][C:20]([Cl:21])=[C:15]([CH2:14][O:13][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[N:3]=[C:2]([CH3:1])[CH:11]=[C:10]3[CH3:12])[C:16]=1[Cl:33])(=[O:24])=[O:23])=[O:29]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 18614Methyl 4-aminobutanoateHCID 181649HOAtHCID 11049469HCID 11049469, compound

Product 1

HCID 54025803HCID 54025803, compoundYield 66.3%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolventHCID 79724-MethylmorpholineSolvent

Procedure

A mixture of 6.85 g (13.4.10-3 mol) of N-[[3-[(2,4-dimethylquinolin-8-yl)oxymethyl]-2,4-dichlorophenyl]sulfonyl]-L-proline, 2.01 g (14.7.10-3 mol) of HOAT and 2.83 g (14.7.10-3 mol) of EDCI in 50 ml of dimethylformamide is prepared. After stirring for 15 min at room temperature, this mixture is added dropwise to a solution of 2.06 g of methyl 4-aminobutyrate (in the form of the hydrochloride) in 35 ml of dimethylformamide and 1.48 ml (13.4.10-3 mol) of N-methylmorpholine. The reaction mixture is stirred for 20 hours at room temperature and 500 ml of dichloromethane are then added, followed by 300 ml of water. After decantation, the organic phase is washed twice with water again, dried over sodium sulfate and then concentrated under reduced pressure. The crude product obtained is purified by chromatography on silica gel using a cyclohexane/ethyl acetate mixture (3/7; v/v) as the eluent to give 5.3 g of the expected product in the form of yellow crystals (yield=64.5%).

Workup

  1. customis prepared
  2. stirringThe reaction mixture is stirred for 20 hours at room temperature
  3. washAfter decantation, the organic phase is washed twice with water again
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product obtained
  7. customis purified by chromatography on silica gel using a cyclohexane/ethyl acetate mixture (3/7; v/v) as the eluent

Sources & evidence

ORD record
ord-99a8d2af2ebd472ba0551d3babd703eb
Source dataset
uspto-grants-2000_05
Patent number
US06063791

Reaction notes

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