2-Fluorobenzothiazole → (1,1-dimethyl ethyl) N-(2-benzothiazolyl)-L-tyrosinate

HRID 1759706Notes

Reaction equation

HRID 1759706 reaction equation
[NH2:1][C@H:2]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.F[C:19]1[S:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1>N1C=CC=CC=1>[S:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[NH:1][C@H:2]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 707532-FluorobenzothiazoleHCID 6950582L-Tyrosine 1,1-dimethylethyl ester

Product 1

HCID 86594975(1,1-dimethyl ethyl) N-(2-benzothiazolyl)-L-tyrosinateYield 62.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture constituted by (1,1-dimethyl ethyl) L-tyrosinate 4-1 (120 mg, 0.5 mmole) and fluorobenzothiazole (75 mg; 0.5 mmole) in 3 ml of pyridine is heated under reflux for 2 hours. The reaction medium is then evaporated under reduced pressure until a dry extracted is obtained which is purified by chromatography eluting with a heptane/ethyl acetate mixture (100/0→0/100). 115 mg of expected product is obtained.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 hours
  3. customThe reaction medium is then evaporated under reduced pressure until a dry
  4. extractionextracted
  5. customis obtained which
  6. customis purified by chromatography
  7. washeluting with a heptane/ethyl acetate mixture (100/0→0/100)

Sources & evidence

ORD record
ord-4505f927674b48e9bbbdc386b3aaf8ce
Source dataset
uspto-grants-2005_01
Patent number
US06838453B2

Reaction notes

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