Hydrochloric Acid → HCID 7023251, compound

HRID 1520601Notes

Reaction equation

HRID 1520601 reaction equation
[NH2:1][C@H:2]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[CH2:3][C:4]([OH:6])=[O:5].[CH2:12]([O:19][C:20](Cl)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O1CCOCC1.Cl>[OH-].[Na+]>[CH2:12]([O:19][C:20]([NH:1][C@H:2]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[CH2:3][C:4]([OH:6])=[O:5])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 312751,4-DioxaneHCID 86716(S)-3-Amino-3-(thiophen-2-yl)propanoic acid

Product 1

HCID 7023251HCID 7023251, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

(S)-3-amino-3-(thiophen-2-yl)propanoic acid (0.894 g) and benzyloxycarbonyl chloride 0.980 g) were stirred in 2M NaOH (8 mL) and dioxane (26 mL) at 0° C. for 24 hours. The reaction mixture was acidified with concentrated aqueous HCl, extracted twice with ethyl acetate, and the extracts were dried over MgSO4, filtered, concentrated, and chromatographed on silica gel with 50% ethyl acetate/hexanes.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialthe extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica gel with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-bcc4755e3d934425b31d428860bc5898
Source dataset
uspto-grants-2015_07
Patent number
US09073855B2

Reaction notes

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