Hydrochloric Acid → HCID 178511762, compound
Reaction equation
NC1SC=[C:5]([C@@H:7]([NH:20]C(C2C=CC3N(C4CCCCC4)C(C4C=COC=4)=NC=3C=2)=O)[CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[N:16]=[N:17][NH:18][N:19]=3)=[CH:11][CH:10]=2)N=1.CCN(C(C)C)C(C)C.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)Cl)C=CC=CC=1.[OH-:72].[Na+].Cl.C1C[O:78]CC1>>[NH:16]1[C:15]([C:12]2[CH:13]=[CH:14][C:9]([CH2:8][C@@H:7]([C:5]([OH:78])=[O:72])[NH2:20])=[CH:10][CH:11]=2)=[N:19][N:18]=[N:17]1Participants
Procedure
The tetrazole compound from above (0.752 g, 2.16 mmol) was dissolved in THF (20 mL) and DIEA (0.75 mL, 4.3 mmol) and triphenylchloromethane (trityl chloride, 0.604 g, 2.16 mmol) were added. The reaction was stirred for 1 h at room temperature and then quenched with 1 N NaOH (13 mL, 13 mmol). After stirring overnight at room temperature, the reaction mixture was cooled in ice and acidified to pH 3-4 with 1 N HCl. The product was extracted into EtOAc (50 mL), washed with brine and the solution dried (Na2SO4). Evaporation of the solvent gave a yellow residue that was purified by passing through a pad of silica gel using EtOAc as eluent. The product was then dissolved in TBME (5 mL) and hexane (10 mL) was added. The precipitated material was collected by filtration and dried to give the desired 4-tetrazolyl-L-phenylalanine free acid as a white solid (0.784 g).
Workup
- stirringAfter stirring overnight at room temperature
- temperaturethe reaction mixture was cooled in ice
- extractionThe product was extracted into EtOAc (50 mL)
- washwashed with brine
- dry with materialthe solution dried (Na2SO4)
- customEvaporation of the solvent
- customgave a yellow residue that
- customwas purified
- dissolutionThe product was then dissolved in TBME (5 mL)
- additionhexane (10 mL) was added
- filtrationThe precipitated material was collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-9501f648f39d4e36bfca14ca73370a8f
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06794404B2
Reaction notes
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