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

HRID 2197269Notes

Reaction equation

HRID 2197269 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-9182f2d9bcaf4dc082e93ae2bf8b64c6
Source dataset
uspto-grants-2012_12
Patent number
US08338471B2

Reaction notes

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