Triethylamine → HCID 70674549, compound

HRID 591300Notes

Reaction equation

HRID 591300 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28]O)=[CH:22][N:21]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[F:44]C(F)(S(F)(=O)=O)C(F)(F)C(F)(F)C(F)(F)F.F.F.F.C(N(CC)CC)C>O1CCCC1.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][F:44])=[CH:22][N:21]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 67814Perfluoro-1-butanesulfonyl fluoride2×HCID 175505N,N-Diethylethanamine trihydrofluoride2×HCID 117812696HCID 117812696, compound

Product 1

HCID 70674549HCID 70674549, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Di-tert-butyl (4R)—N-(tert-butoxycarbonyl)-4-{[5-(3-hydroxypropyl)pyridin-2-yl]methyl}-L-glutamate (68 mg, 0.13 mmol) was dissolved in 2 ml tetrahydrofuran, and cooled to 0° C. Triethylamine (280 μl, 2.01 mmol), 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (162 mg, 0.53 mmol), and triethylamine trihydrofluoride (86 mg, 0.53 mmol) were added, and the reaction was stirred at room temperature for 24 h. The same amounts of triethylamine, 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride and triethylamine trihydrofluoride were added again and the reaction was continued for 1 h. Water (10 ml) was added, and the mixture was extracted with dichloromethane (3×10 ml). The organic phases were dried over magnesium sulfate and concentrated. The so derived material was used without further purification.

Workup

  1. waitthe reaction was continued for 1 h
  2. extractionthe mixture was extracted with dichloromethane (3×10 ml)
  3. dry with materialThe organic phases were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customwas used without further purification

Sources & evidence

ORD record
ord-d6b6eb7f846b4328b221bf0798ab6e83
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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