Formaldehyde → HCID 819481, compound

HRID 373649Notes

Reaction equation

HRID 373649 reaction equation
[C:1]([NH:11][C@H:12]([C:20]([OH:22])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C=O.[C:25]1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:4]([O:3][C:1]([N:11]1[C@@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20](=[O:22])[O:21][CH2:25]1)=[O:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 70878Benzyloxycarbonyl-L-phenylalanine

Product 1

HCID 819481HCID 819481, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Following the procedure of Ben-Ishai (J. Am. Chem. Soc., 1957, 79, 5736), N-Cbz-L-phenylalanine (10.0 gm, 33.4 mmol), paraformaldehyde (3.0 gm, 100.2 mmol), and p-toluenesulfonic acid (0.64 gm, 3.3 mmol) were suspended in toluene (150 ml). The reaction was brought to reflux and water removed azeotropically through the agency of a Dean-Stark trap until collection of water ceased (0.5-2.0 h). After cooling, the reaction mixture was diluted with ethyl ether, washed (1X, saturated aqueous NaHCO3 ; 1X, brine), dried (Na2SO4), filtered, and concentrated in vacuo to provide a solid after cooling. Recrystallization from ethyl acetate/hexanes provided, after the collection of two crops, the pure title compound (9.26 gm, 89%). m.p.=85.5°-86.5° C.; MS (CI) (M+NH4)+ =329, (M+H)+ =312; Anal. Calcd. for C18H17NO4 : C, 69.44; H, 5.50; N, 4.50. Found: C, 69.33; H, 5.48; N, 4.40.

Workup

  1. temperatureto reflux
  2. customwater removed azeotropically through the agency of a Dean-Stark trap until collection of water
  3. custom(0.5-2.0 h)
  4. temperatureAfter cooling
  5. additionthe reaction mixture was diluted with ethyl ether
  6. washwashed (1X, saturated aqueous NaHCO3 ; 1X, brine)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto provide a solid
  11. temperatureafter cooling
  12. customRecrystallization from ethyl acetate/hexanes
  13. customprovided
  14. customafter the collection of two crops

Sources & evidence

ORD record
ord-8447760923f34b34afa5d4ff414eae08
Source dataset
uspto-grants-1992_11
Patent number
US05164388

Reaction notes

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