N-[tert-butoxycarbonyl]-L-serine → HCID 178454224, compound

HRID 1424182Notes

Reaction equation

HRID 1424182 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13]O)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(N(C)C)=[N+]1C2C(=NC=CC=2)[N+]([O-])=N1)C.F[P-](F)(F)(F)(F)F.[C:39]([C:43]1[CH:44]=[C:45]([NH2:50])[C:46]([NH2:49])=[CH:47][CH:48]=1)([CH3:42])([CH3:41])[CH3:40]>CN(C)C=O.O>[C:39]([C:43]1[CH:48]=[CH:47][C:46]2[NH:49][C:13]([C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][OH:12])=[N:50][C:45]=2[CH:44]=1)([CH3:42])([CH3:40])[CH3:41]

Participants

6

Reactant 3

HCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 4327084-Tert-butylbenzene-1,2-diamineHCID 178484293HCID 178484293, compound

Product 1

HCID 178454224HCID 178454224, compoundYield 21.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxypropanoic acid (226 mg, 1.10 mmol) was dissolved in N,N-dimethylformamide (5 mL) and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxid-hexafluorophosphate (440 mg, 1.10 mmol) was added. The reaction was stirred for 10 minutes then 4-(tert-butyl)benzene-1,2-diamine (164 mg, 1.00 mmol) was added and the reaction mixture stirred for 18 hours. The reaction mixture was diluted with water and extracted twice with ethyl ether. The combined organic phase was dried over anhydrous magnesium sulfate, filtered and the solvent removed in vacuo. The residue was dissolved in 1,2-dichloroethane and anhydrous magnesium sulfate was added. The reaction was stirred at 65° C. for 18 hours to complete the dehydration. The reaction mixture was filtered and loaded directly onto a 4 g silica gel column for purification. The column was eluted with 0-10% methanol in dichloromethane to afford 73 mg of product as a white solid.

Workup

  1. stirringthe reaction mixture stirred for 18 hours
  2. extractionextracted twice with ethyl ether
  3. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. dissolutionThe residue was dissolved in 1,2-dichloroethane
  7. additionanhydrous magnesium sulfate was added
  8. stirringThe reaction was stirred at 65° C. for 18 hours
  9. filtrationThe reaction mixture was filtered
  10. customloaded directly onto a 4 g silica gel column for purification
  11. washThe column was eluted with 0-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-0583c26fc47647cf9fcce7f0c4b09836
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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