L-Tyrosine 1,1-dimethylethyl ester → tert-butyl (2S)-2-[[4-(dihexylamino)-1,1-dioxo-1,2,5-thiadiazol-3-yl]amino]-3-(4-hydroxyphenyl)propanoate

HRID 1821077Notes

Reaction equation

HRID 1821077 reaction equation
[CH2:1]([N:7]([C:14]1[C:15](OCC)=[N:16][S:17](=[O:20])(=[O:19])[N:18]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:24]([O:28][C:29](=[O:40])[C@H:30]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)[NH2:31])([CH3:27])([CH3:26])[CH3:25]>CCO>[C:24]([O:28][C:29](=[O:40])[C@H:30]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)[NH:31][C:15]1[C:14]([N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[N:18][S:17](=[O:19])(=[O:20])[N:16]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 6950582L-Tyrosine 1,1-dimethylethyl esterHCID 221387874-(N,N-di-n-hexylamino)-3-ethoxy-1,1-dioxo-1,2,5-thiadiazole

Product 1

HCID 178444783tert-butyl (2S)-2-[[4-(dihexylamino)-1,1-dioxo-1,2,5-thiadiazol-3-yl]amino]-3-(4-hydroxyphenyl)propanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(N,N-di-n-hexylamino)-3-ethoxy-1,1-dioxo-1,2,5-thiadiazole (400 mg, 1.02 mmol) and L-tyrosine t-butyl ester (261 mg, 1.1 mmol) in EtOH (10 mL) was stirred at room temperature for 36 hrs. The solvent was removed under reduced pressure residue purified by flash column chromatography (silica, hexane:EtOAc 3:1 then 1:1) to give the title compound as a white waxy solid (400 mg, 73%).

Workup

  1. customThe solvent was removed under reduced pressure residue
  2. custompurified by flash column chromatography (silica, hexane:EtOAc 3:1

Sources & evidence

ORD record
ord-caad4eab345f43568f77c49893c31d40
Source dataset
uspto-grants-2009_10
Patent number
US07605166B2

Reaction notes

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