Triethylamine → HCID 43405688, compound

HRID 2217320Notes

Reaction equation

HRID 2217320 reaction equation
Cl.[NH2:2][CH:3]([C:6]([OH:8])=[O:7])[CH2:4][OH:5].[CH2:9](N(CC)CC)C.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25](Cl)=[O:26])=[CH:20][CH:19]=1>ClCCl>[CH3:9][O:7][C:6](=[O:8])[CH:3]([NH:2][C:25](=[O:26])[CH2:24][C:21]1[CH:22]=[CH:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=1)[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27346884-Methoxyphenylacetyl chlorideHCID 12219628HCID 12219628, compound

Product 1

HCID 43405688HCID 43405688, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

to a suspension of DL-serine HCl (2.0 g, 12.8 mmol) in dichloromethane (10 mL) at 0° C. were added dropwise triethylamine (3.58 mL, 25.7 mmol) and (4-methoxyphenyl)-acetyl chloride (1.96 mL, 12.8 mmol). The mixture was stirred at 25° C. for 12 hours. The reaction mixture was washed with a saturated aqueous sodium chloride solution, separated, and evaporated to dryness and purified by column chromatography (hexanes: ethyl acetate from 25 to 100%). 3-Hydroxy-2-[2-(4-methoxy-phenyl)-acetylamino]-propionic acid methyl ester was isolated as a white solid (2g, 58%). ESI-MS m/z calc. 267.3, found 268.2 (M+1)+. Retention time of 1.83 minutes. 1H NMR (400 MHz, CDCl3) δ3.64 (s, 2H), 3.78 (s, 3H), 3.83 (s, 3H), 3.93 (qd, J=14.6 and 4.0 Hz, 2H), 4.66 (m, 1H), 6.40 (m, 1H), 7.01 (d, J=8.7 Hz, 2H), 7.23 (d, J=8.7 Hz, 2H).

Workup

  1. washThe reaction mixture was washed with a saturated aqueous sodium chloride solution
  2. customseparated
  3. customevaporated to dryness
  4. custompurified by column chromatography (hexanes: ethyl acetate from 25 to 100%)

Sources & evidence

ORD record
ord-631e36022e0740faaa1ec0949463532f
Source dataset
uspto-grants-2008_08
Patent number
US07407976B2

Reaction notes

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