Trifluoroacetic acid → HCID 89668483, compound

HRID 1482388Notes

Reaction equation

HRID 1482388 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][C:25]1[N:26]=[CH:27][S:28][CH:29]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[CH:13]1[C:12]2[CH:11]([CH2:10][O:9][C:7]([N:4]([CH3:5])[C@@H:3]([CH2:24][C:25]3[N:26]=[CH:27][S:28][CH:29]=3)[C:2]([OH:6])=[O:1])=[O:8])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=2[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 89668532HCID 89668532, compound

Product 1

HCID 89668483HCID 89668483, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

(S)-(9H-Fluoren-9-yl)methyl 5-oxo-4-(thiazol-4-ylmethyl)oxazolidine-3-carboxylate (Compound SP817) (40.0 g, 98.4 mmol), trifluoroacetic acid (245 ml, 3.18 mol) and triethylsilane (160 ml, 1.00 mol) were dissolved in dichloromethane (1 l) under a nitrogen atmosphere, and the mixture was stirred at 35° C. for two days. The reaction solution was concentrated under reduced pressure and then dissolved in diethyl ether, and the organic layer was washed with an aqueous sodium bicarbonate solution. The aqueous layer was adjusted to pH 3 with a aqueous potassium bisulfate solution and extracted with dichloromethane. All organic extracts obtained were washed with brine, dried over sodium sulfate and then concentrated under reduced pressure to afford (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-(thiazol-4-yl)propanoic acid (Compound SP811, Fmoc-MeAla(4-Thz)-OH) (35 g, 87%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutiondissolved in diethyl ether
  3. washthe organic layer was washed with an aqueous sodium bicarbonate solution
  4. extractionextracted with dichloromethane
  5. customAll organic extracts obtained
  6. washwere washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-057fa5b9473940b2a9187df32bb5e2a5
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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