Hydrochloric Acid → HCID 43405688, compound

HRID 2261272Notes

Reaction equation

HRID 2261272 reaction equation
[NH2:1][CH:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].Cl.[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:6][C:5](=[O:7])[CH:2]([NH:1][C:25](=[O:26])[CH2:24][C:21]1[CH:22]=[CH:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=1)[CH2:3][OH:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 617DL-SerineHCID 8471TriethylamineHCID 27346884-Methoxyphenylacetyl chloride

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 (2 g, 58%). ESI-MS m/z calc. 267.3, found 268.2 (M+1)+. Retention time of 1.83 minutes. 1H NMR (400 MHz, CDCl3) δ 3.64 (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-e86f958b0a7d46fa94e89da60228a05d
Source dataset
uspto-grants-2010_12
Patent number
US07846951B2

Reaction notes

Loading…