Ethylene Glycol → HCID 69677444, compound

HRID 966409Notes

Reaction equation

HRID 966409 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:16]=[CH:15][C:8]([CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])=[CH:7][CH:6]=1)([O-:4])=[O:3].[CH2:17](O)[CH2:18][OH:19]>>[ClH:1].[OH:19][CH2:18][CH2:17][O:13][C:12](=[O:14])[C@H:10]([CH2:9][C:8]1[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:16][CH:15]=1)[NH2:11]

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 137064-Nitro-3-phenyl-L-alanine

Product 1

HCID 69677444HCID 69677444, compoundYield 73.9%

Conditions

Temperature
82.5 °C

Procedure

Dry hydrogen chloride (68.3 g) was dissolved in ethylene glycol (994 mL) at <20° C. and then solid 4-nitro-(S)-phenylalanine (198.7 g) added with stirring. The mixture was heated to 80-85° C. and held at this temperature for 2 h. After a LC completion check, the preparation was allowed to drift to 60° C. and seeded with authentic product. Once crystallisation had initiated, the resulting suspension was cooled further to 20° C. and stirred out overnight. The 4-nitro(S)-phenylalanine hydroxyethyl ester hydrochloride was collected by filtration, washed in situ with dimethoxyethane (795 mL), and then dried in vacuo at 40-45° C. to constant weight (white powder m.p. 195-197° C., 187.0 g, 73.9% yield). 1H NMR (D6-DMSO): δ3.27 (2H, ddd); 3.42 (2H, m); 4.01 (2H, m); 4.27 (1H, t); 4.88 (1H, b,s); 7.52 (2H, d); 8.11 (2H, d); 8.76 (3H, b,s) ppm. Mass Spectrum: ESI+ (m/z+1) 255.0

Workup

  1. customto drift to 60° C.
  2. customOnce crystallisation
  3. temperaturethe resulting suspension was cooled further to 20° C.
  4. stirringstirred out overnight
  5. filtrationThe 4-nitro(S)-phenylalanine hydroxyethyl ester hydrochloride was collected by filtration
  6. washwashed in situ with dimethoxyethane (795 mL)

Sources & evidence

ORD record
ord-0749169e218c421d8d0fb4a895a74162
Source dataset
uspto-grants-2005_10
Patent number
US06951943B2

Reaction notes

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