3-Chlorobenzoic Acid → HCID 43405659, compound

HRID 732052Notes

Reaction equation

HRID 732052 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.Cl.[CH3:12][O:13][C:14](=[O:19])[C@H:15]([CH2:17][OH:18])[NH2:16].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.CCN=C=NCCCN(C)C>CN(C=O)C.C(OCC)(=O)C>[CH3:12][O:13][C:14](=[O:19])[CH:15]([NH:16][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=1)[CH2:17][OH:18]

Participants

8

Reactant 5

HCID 4473-Chlorobenzoic AcidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Product 1

HCID 43405659HCID 43405659, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 3-Chlorobenzoic acid (5.0 g, 31.9 mmol), serine methylester hydrochloride (6.1 g, 31.9 mmol) and HOBt (4.31 g, 31.9 mmol) in DMF (100 ml) was added N-methylmorpholine (NMM) (7.0 ml, 63.8 mmol) and EDCI (4.97 g, 31.9 mmol) at 0° C. The mixture was allowed to warm to room temperature and stirred for 18 h. The mixture was diluted with ethyl acetate (300 ml) and then washed with water (3×250 ml) followed by brine. The organic extract was dried over Na2SO4 (anhydrous) and then concentrated in vacuo giving 2-(3-Chloro-benzoylamino)-3-hydroxy-propionic acid methyl ester (7.2 g, 93%) of a pale yellow solid. 1H NMR (CDCl3) d (ppm): 7.78 (s, 1 H), 7.66 (d, 1 H), 7.45, (dd, 1 H), 7.34 (t, 1 H), 7.25 (br, d, 1H), 4.82 (m, 1 H), 4.08 (m, 2 H), 3.79 (s, 3 H), 3.19 (br, t, 1H).

Workup

  1. washwashed with water (3×250 ml)
  2. extractionThe organic extract
  3. dry with materialwas dried over Na2SO4 (anhydrous)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3e8e18bc0d174c7dbf227f87b921d488
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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