Hydrochloric Acid → N-Boc-O-(4-bromophenyl)-L-serine

HRID 910417Notes

Reaction equation

HRID 910417 reaction equation
C[O:2][C:3](=[O:22])[CH:4]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1.O[Li].O.Cl>C1COCC1.O>[Br:13][C:10]1[CH:9]=[CH:8][C:7]([O:6][CH2:5][CH:4]([NH:14][C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[C:3]([OH:22])=[O:2])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 666610643-(4-Bromophenoxy)-2-tert-butoxycarbonylamino-propionic acid methyl ester2×

Product 1

HCID 66660912N-Boc-O-(4-bromophenyl)-L-serineYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound obtained in step d above (22d) (1.087 g, 2.91 mmol) in THF (40 mL) at 0° C. was added a solution of LiOH H2O (244 mg, 5.82 mmol) in water (10 mL). After being stirred for 6 h, 0.5 N HCl (5 mL) was added and the reaction was concentrated under vacuum. The residue was diluted with EtOAc and washed with brine. The combined organic layers were dried over Na2SO4 and concentrated; the residue was purified by silica gel column chromatography to give the title compound as a colourless oil (816 mg, 78% yield).

Workup

  1. concentrationthe reaction was concentrated under vacuum
  2. additionThe residue was diluted with EtOAc
  3. washwashed with brine
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-39f4d711492d4baca7da1391521a3f00
Source dataset
uspto-grants-2011_09
Patent number
US08022092B2

Reaction notes

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