HCID 67169758, compound → HCID 57331880, compound

HRID 919026Notes

Reaction equation

HRID 919026 reaction equation
[OH:1][CH:2]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[CH:3]1[CH2:7][O:6]C(C)(C)[N:4]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]>CO>[OH:1][C@H:2]([C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)[C@H:3]([NH:4][C:10](=[O:11])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:7][OH:6]

Participants

3

Reactant 1

HCID 67169758HCID 67169758, compound

Product 1

HCID 57331880HCID 57331880, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of benzyl 4-(hydroxy-(4-methoxyphenyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate (1.679 g, 4.5 mmol) and amberlyst 15 (1.85 g) in MeOH (20 mL) was stirred at room temperature for 2 days. The mixture was centrifuged and the solid was washed with MeOH (2×40 mL). The solvent was removed to dryness and after purification by column chromatography (SiO2 using a mixture of CH2Cl2/EtOAc) the product was obtained as a white solid (1.26 g, 84% yield).

Workup

  1. washthe solid was washed with MeOH (2×40 mL)
  2. customThe solvent was removed to dryness
  3. customafter purification by column chromatography (SiO2 using
  4. additiona mixture of CH2Cl2/EtOAc) the product

Sources & evidence

ORD record
ord-826d65cd4235415b8715f8cb2ec8594b
Source dataset
uspto-grants-2016_03
Patent number
US09272996B2

Reaction notes

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