Diisopropylethylamine → (S)-2-(2-Allyloxy-benzoylamino)-3-(4-allyloxy-3-chloro-phenyl)-propionic acid methyl ester

HRID 928222Notes

Reaction equation

HRID 928222 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C@H:12]([NH2:17])[C:13]([O:15][CH3:16])=[O:14])=[CH:7][C:6]=1[Cl:18])[CH:2]=[CH2:3].[CH2:19]([O:22][C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](O)=[O:26])[CH:20]=[CH2:21].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.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:16][O:15][C:13](=[O:14])[C@@H:12]([NH:17][C:25](=[O:26])[C:24]1[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=1[O:22][CH2:19][CH:20]=[CH2:21])[CH2:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[C:6]([Cl:18])[CH:7]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 37987032-(Allyloxy)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86691117(S)-methyl 3-(4-(allyloxy)-3-chlorophenyl)-2-aminopropanoate

Product 1

HCID 86691118(S)-2-(2-Allyloxy-benzoylamino)-3-(4-allyloxy-3-chloro-phenyl)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
22 °C

Procedure

In a 10 mL round-bottomed flask, (S)-methyl 3-(4-(allyloxy)-3-chlorophenyl)-2-aminopropanoate (65 mg, 241 μmol, Eq: 1.00) was combined with DMF (2 mL) to give a colorless solution. 2-(allyloxy)benzoic acid (54.2 mg, 289 μmol, Eq: 1.20), HATU (183 mg, 482 μmol, Eq: 2.00) and Hunig's base (62.3 mg, 84.2 μL, 482 μmol, Eq: 2.00) were added. The reaction mixture was stirred at 22° C. for 16 h. The reaction mixture was poured into saturated aqueous NaHCO3 solution and extracted with DCM (2×). The organic layers were combined, washed with 0.1M aqueous HCl (1×), water (3×), and brine (1×). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 10 g, n-heptane/AcOEt 4/1) to yield a light yellow oil (96 mg; 93%). m/z=430.2 [M+H]+.

Workup

  1. customto give a colorless solution
  2. extractionextracted with DCM (2×)
  3. washwashed with 0.1M aqueous HCl (1×), water (3×), and brine (1×)
  4. dry with materialThe organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (silica gel, 10 g, n-heptane/AcOEt 4/1)
  7. customto yield a light yellow oil (96 mg; 93%)

Sources & evidence

ORD record
ord-0baac7c0c79a4c73ac07d52812bd9324
Source dataset
uspto-grants-2016_03
Patent number
US09290467B2

Reaction notes

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