Anisole → HCID 90060127, compound

HRID 1779163Notes

Reaction equation

HRID 1779163 reaction equation
C1(OC)C=CC=CC=1.Cl.[NH2:10][C@@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]#[C:29][CH3:30])=[CH:22][CH:21]=1)[C:12]([O:14]C(C)(C)C)=[O:13]>C(O)=O>[NH2:10][C@@H:11]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:27][C:28]#[C:29][CH3:30])=[CH:24][CH:25]=1)[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 7519AnisoleHCID 67269329HCID 67269329, compound

Product 1

HCID 90060127HCID 90060127, compoundYield 129.9%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Formic acid (5 mL), and anisole (20 μL) were added to tert-butyl (S)-2-amino-3-(4-but-2-ynyloxy-phenyl)-propionate HCl salt (200 mg) and the mixture was stirred at room temperature for 18 hours. Completion of the reaction was confirmed by detecting the target product by LCMS (LCMS m/z 234 (M+1), Rt 0.83 min.). The reaction solution was concentrated under reduced pressure to obtain (S)-2-amino-3-(4-but-2-ynyloxy-phenyl)-propionic acid (186 mg).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d59add00c54a4e8fa8d99ccdbe166b94
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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