Tyramine → tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamate

HRID 130811Notes

Reaction equation

HRID 130811 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[O:11](C(OC(C)(C)C)=O)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=O>C1COCC1>[C:15]([O:14][C:12](=[O:11])[NH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 5610TyramineHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 11831452tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Suspend tyramine (10.0 g, 73.0 mmol) in THF (200 mL). Cool to 0° C. Add a solution of (BOC)2O (31.8 g, 145 mmol) in THF (43 mL). Allow reaction mixture to warm to room temperature overnight. After 20 hours concentrate. Purification through two Waters 500A columns on a PrepLC system 500A to give the title compound: MS FAB ES+ 238.3 (M+H)+, base peak 182.2 (M+2H—C(CH3)3)+; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), acetonitrile in water containing 0.01% concentrated HCl at 1.0 mL/min, 30-99% over 19 min], tR=8.5 min, 100% purity.

Workup

  1. customAllow reaction mixture
  2. temperatureto warm to room temperature overnight
  3. concentrationAfter 20 hours concentrate
  4. customPurification through two Waters 500A columns on a PrepLC system 500A

Sources & evidence

ORD record
ord-f6b38d578ea440fb8fe8f987aad444f2
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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