Allyl bromide → (S)-3-(Allyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

HRID 633787Notes

Reaction equation

HRID 633787 reaction equation
[CH2:1]([O:4][CH2:5][C@H:6]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:7]([O:9]C)=[O:8])[CH:2]=[CH2:3].BrCC=C>C(Cl)Cl>[CH2:1]([O:4][CH2:5][C@H:6]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:7]([OH:9])=[O:8])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 57846413(S)-3-Allyloxy-2-tert-butoxycarbonylamino-propionic acid methyl ester

Product 1

HCID 11032134(S)-3-(Allyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-methyl 3-(allyloxy)-2-(tert-butoxycarbonylamino)propanoate (200 mg, 0.91 mmol) and 3-bromoprop-1-ene (552 mg, 4.56 mmol) were dissolved in DCM (10 mL). Then Ag2O (654 mg, 2.74 mmol) was added at the room temperature. After stirring for 3 hours, the mixture was filtered, concentrated and purified by flash column chromatography to give the title compound A6-1 (149 mg, 63.1%) as light yellow oil.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated
  3. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-e86ea88222ee4670b32f9974a183bf83
Source dataset
uspto-grants-2016_04
Patent number
US09321809B2

Reaction notes

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