Hydrochloric Acid → HCID 131714611, compound

HRID 980408Notes

Reaction equation

HRID 980408 reaction equation
[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:2]([C:11]([CH:13]=[N+]=[N-])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[ClH:23]>O1CCCC1>[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:2]([C:11]([CH2:13][Cl:23])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131714612HCID 131714612, compound

Product 1

HCID 131714611HCID 131714611, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Boc-TyrCHN2 (1.81 g, 5.92 mmol) was dissolved in 30 mL of tetrahydrofuran, and the resulting solution wwas treated with 3.45N ethanolic:HCl (1.72 mL, 5.92 mmol) for 5 minutes at 0°. Solvent was removed by evaporation on a rotary evaporator without temperature regulation. The remaining residue was dissolved in ethyl acetate, and the resulting solution was washed with 0.2N hydrochloric acid followed by saturated aqueous sodium chloride. The washed solution was dried over sodium sulfate, and then solvent was evaporated to yield crystalline Boc-TyrCH2Cl. Crystals were isolated and washed with cold ether to yield 0.45 g (m.p. 110°-112°) in a first crop, and 0.90 g (m.p. 110°-112°) in a second crop. NMR spectra in CDCl3 corresponded to that expected, except that methylene protons of --COCH2Cl appears as a doublet at δ4.1.

Workup

  1. additionthe resulting solution wwas treated with 3.45N ethanolic
  2. customSolvent was removed by evaporation on a rotary evaporator without temperature regulation
  3. dissolutionThe remaining residue was dissolved in ethyl acetate
  4. washthe resulting solution was washed with 0.2N hydrochloric acid
  5. dry with materialThe washed solution was dried over sodium sulfate
  6. customsolvent was evaporated

Sources & evidence

ORD record
ord-ec29674cf12c4a30a67f3d354a64474d
Source dataset
uspto-grants-1987_01
Patent number
US04636492

Reaction notes

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