Hydrochloric Acid → Boc-homophenylalaninal

HRID 1595145Notes

Reaction equation

HRID 1595145 reaction equation
N1(C(N[C@H](C(O)=O)[CH2:11][C:12]2[CH:17]=CC=C[CH:13]=2)=O)CCOCC1.CN1CC[O:25]CC1.Cl[C:29]([O:31]CC(C)C)=[O:30].Cl.[NH2:37][C@@H:38]([CH2:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH:39]=CC(OCC)=O.Cl>C1COCC1.CN(C=O)C>[C:29]([NH:37][C@H:38]([CH:39]=[O:25])[CH2:46][CH2:47][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)([O:31][C:12]([CH3:11])([CH3:13])[CH3:17])=[O:30]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 664657CP 84364HCID 86754733ethyl (S)-4-amino-6-phenyl-2-hexenoate hydrochloride

Product 1

HCID 10264740Boc-homophenylalaninalYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Morpholinecarbonylphenylalanine (2.74 g, 9.82 mmol, prepared according to the method described in Esser, R. et.al., Arthritis & Rheumatism (1994), 0000) was dissolved in THF (50 mL) at −10° C. 4-methylmorpholine (1.08 mL, 9.82 mmol) was added, followed by isobutyl chloroformate (1.27 mL, 9.82 mmol). The mixed anhydride was stirred for 10 minutes, whereupon a solution of ethyl (S)-4-amino-6-phenyl-2-hexenoate hydrochloride from the previous step in DMF (10 mL) was added, followed by 4-methylmorpholine (1.08 mL, 9.82 mmol). The mixture was stirred for 1 hour. 1M HCl (50 mL) was added. The product was extracted with ethyl acetate (100 mL), washed with saturated aqueous NaHCO3 (50 mL), dried over MgSO4 and decolorizing charcoal (DARCO), filtered, and evaporated to dryness, giving 3.80 g (80% yield from Boc-homophenylalaninal).

Workup

  1. additionwas added
  2. extractionThe product was extracted with ethyl acetate (100 mL)
  3. washwashed with saturated aqueous NaHCO3 (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-2223d055049e41c1a37c87f1d8e69ad7
Source dataset
uspto-grants-2001_09
Patent number
US06287840B1

Reaction notes

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