Hydrochloric Acid → 2-Amino-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester

HRID 479126Notes

Reaction equation

HRID 479126 reaction equation
[CH2:1]([O:3][C:4](=[O:46])[CH:5]([N:32]=C(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH2:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:23][C:24]=2[CH3:25])=[CH:9][CH:8]=1)[CH3:2].Cl>C1COCC1>[CH2:1]([O:3][C:4](=[O:46])[CH:5]([NH2:32])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH2:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:23][C:24]=2[CH3:25])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 865874772-(Benzhydrylidene-amino)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester

Product 1

HCID 695578292-Amino-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The above prepared 2-(benzhydrylidene-amino)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester was dissolved in 20 ml of THF and treated at 0° with 5 ml of 2N HCl. The cleavage of the protecting group was monitored by TLC. After 5 h the reaction mixture was poured onto crushed ice/NaHCO3 and extracted twice with AcOEt, washed with water, dried over sodium sulfate, and the solvents were removed i.V. Flash chromatography (SiO2, AcOEt) produced 0.505 g of the title compound as colorless oil.

Workup

  1. additionAfter 5 h the reaction mixture was poured
  2. extractionextracted twice with AcOEt
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvents were removed i.V

Sources & evidence

ORD record
ord-f90d0c62145849d690102982cf05f649
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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