Hydrochloric Acid → HCID 86679572, compound

HRID 1776611Notes

Reaction equation

HRID 1776611 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][CH:16]=1)[C:10]([O:12]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][CH:16]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 46181731HCID 46181731, compound

Product 1

HCID 86679572HCID 86679572, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(methylsulfonyloxy)phenyl)-propanoate (300 mg, 0.8 mmol) was dissolved in THF (5 ml), and LiOH 1M (2 ml) was added. The mixture was stirred at RT for 5 hours, then HCl 1M was added, and the product was extracted with EtOAc. The organic layer was dried over Na2SO4 and evaporated under vacuum to give 229 mg (80%) of the title compound which was employed in the next step without any further purification. MS/ESI+ 360.39 [MH]+.

Workup

  1. extractionthe product was extracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-5128afe79a134c21a590e2948e5eab68
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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