Nitrogen → HCID 90456988, compound

HRID 625886Notes

Reaction equation

HRID 625886 reaction equation
[O:1]=[C:2]1[O:6][CH2:5][N:4]([C:7]([O:9][CH2:10][CH:11]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=3)=[O:8])[C@H:3]1[CH2:24][O:25][C:26]1[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O.N#N>C(Cl)(Cl)Cl.CCOC(C)=O>[CH:22]1[C:23]2[CH:11]([CH2:10][O:9][C:7]([N:4]([CH3:5])[C@@H:3]([CH2:24][O:25][C:26]3[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=3)[C:2]([OH:6])=[O:1])=[O:8])[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]=2[CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 90457267HCID 90457267, compound

Product 1

HCID 90456988HCID 90456988, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-(9H-fluoren-9-yl)methyl 5-oxo-4-((m-tolyloxy)methyl)oxazolidine-3-carboxylate (825 mg, 1.921 mmol) was dissolved in CHCl3 (10 mL) and added triethylsilane (1.534 ml, 9.60 mmol) followed by TFA (10 ml, 130 mmol) and stirred at RT under positive pressure of N2 for 18 hrs. The reaction was then evaporated on rotovap until a sticky oil was left behind. The oil was dissolved in EtOAc and then extracted with sat. sodium bicarbonate (10 ml×2). There was a middle layer between the aqueous layer and organic layer that appeared to be the deprotonated product. The aqueous layer and middle layer were separated and collected and then acidified until pH 4-5. The solution formed a precipitate once acidic. EtOAc (200 ml) was used to extract the precipitate. The organic layer washed with brine, collected, dried over MgSO4, filtered and evaporated to get the pure product (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-(m-tolyloxy)propanoic acid (506 mg, 1.173 mmol, 61.0% yield) as a white solid. ESI-MS (+) m/z=454 (M+Na)

Workup

  1. customThe reaction was then evaporated on rotovap until a sticky oil
  2. waitwas left behind
  3. dissolutionThe oil was dissolved in EtOAc
  4. extractionextracted with sat. sodium bicarbonate (10 ml×2)
  5. customThe aqueous layer and middle layer were separated
  6. customcollected
  7. customThe solution formed a precipitate once acidic
  8. extractionto extract the precipitate
  9. washThe organic layer washed with brine
  10. customcollected
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. customevaporated

Sources & evidence

ORD record
ord-c74d401499d04074b1bee088c215387f
Source dataset
uspto-grants-2016_04
Patent number
US09308236B2

Reaction notes

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