Hydrochloric Acid → HCID 131714611, compound

HRID 1380607Notes

Reaction equation

HRID 1380607 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 mmoles) was dissolved in 30 mL of tetrahydrofuran, and the resulting solution was treated with 3.45N ethanolic HCl (1.72 mL, 5.92 mmoles) for 5 minutes at 0°. Solvent was removed by evaporation on a rotary evaporator without temperature regulation. The resulting residue was dissolved in ethyl acetate, and this solution was washed with 0.2N hydrochloric acid and saturated sodium chloride. The solution was dried over sodium sulfate, and solvent was evaporated to yield crystalline Boc-TyrCH2Cl. The crystals were isolated and washed with cold ether to yield 0.45 g (mp 110°-112°). In a second crop, 0.90 g (mp 110°-112°) was obtained. NMR in CDCl3 corresponded to that expected, except that methylene protons of --COCH2Cl appeared as a doublet at δ4.1.

Workup

  1. customSolvent was removed by evaporation on a rotary evaporator without temperature regulation
  2. dissolutionThe resulting residue was dissolved in ethyl acetate
  3. washthis solution was washed with 0.2N hydrochloric acid and saturated sodium chloride
  4. dry with materialThe solution was dried over sodium sulfate, and solvent
  5. customwas evaporated

Sources & evidence

ORD record
ord-3629e7b61cf3485599962970a8ce25cb
Source dataset
uspto-grants-1986_04
Patent number
US04582821

Reaction notes

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