5-Tert-butylthiophene-2-carboxylic acid → tert-butyl (5-(tert-butyl)thiophene-2-carbonyl)-L-tyrosinate

HRID 1775831Notes

Reaction equation

HRID 1775831 reaction equation
[C:1]([C:5]1[S:9][C:8]([C:10]([OH:12])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:37][C@@H:38]([CH2:46][C:47]1[CH:52]=[CH:51][C:50]([OH:53])=[CH:49][CH:48]=1)[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40]>CN(C=O)C>[C:1]([C:5]1[S:9][C:8]([C:10]([NH:37][C@H:38]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:46][C:47]2[CH:52]=[CH:51][C:50]([OH:53])=[CH:49][CH:48]=2)=[O:12])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 4583495-Tert-butylthiophene-2-carboxylic acidHCID 6950582L-Tyrosine 1,1-dimethylethyl esterHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86689678tert-butyl (5-(tert-butyl)thiophene-2-carbonyl)-L-tyrosinateYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared using General Procedure 7. Into a solution of 5-(tert-butyl)thiophene-2-carboxylic acid (1.93 g, 10.0 mmol) in DMF (20 mL) were added HATU (4.56 g, 12.0 mmol) and TEA (4.18 mL, 30.0 mmol). The mixture was stirred at room temperature for 30 min and (S)-tert-butyl 2-amino-3-(4-hydroxyphenyl)propanoate (2.37 g, 10.0 mmol) was added. After 1 h, the reaction mixture was poured into 400 mL of ice-water and the solid was filtered. The solid was dissolved in DCM and EA, dried over MgSO4, concentrated, and purified by chromatography (EA/hexanes) to provide 3.6 g (89%) of tert-butyl (5-(tert-butyl)thiophene-2-carbonyl)-L-tyrosinate. LCMS-ESI (m/z) calculated for C22H29NO4S: 403.2. found: 426.1 [M+Na]+, tR=9.07 min (Method 2).

Workup

  1. customPrepared
  2. waitAfter 1 h
  3. filtrationthe solid was filtered
  4. dissolutionThe solid was dissolved in DCM
  5. dry with materialEA, dried over MgSO4
  6. concentrationconcentrated
  7. custompurified by chromatography (EA/hexanes)

Sources & evidence

ORD record
ord-4383e591810a4a0db9aa407d477f2444
Source dataset
uspto-grants-2016_02
Patent number
US09260427B2

Reaction notes

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