Trifluoroacetic acid → HCID 178443077, compound

HRID 926806Notes

Reaction equation

HRID 926806 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].C([SiH](C(C)C)C(C)C)(C)C.[NH:18]([C:56]([CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH3:72])=[O:57])[CH2:19][C:20]([NH:22][C@H:23]([C:49]([O:51]C(C)(C)C)=[O:50])[CH2:24][C:25]1[N:29]=[CH:28][N:27](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:26]=1)=[O:21]>O>[NH:18]([C:56]([CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH3:72])=[O:57])[CH2:19][C:20]([NH:22][C@H:23]([C:49]([OH:51])=[O:50])[CH2:24][C:25]1[N:29]=[CH:28][NH:27][CH:26]=1)=[O:21].[F:4][C:3]([C:1]([OH:7])=[O:2])([F:6])[F:5]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 138754Silane, tris(1-methylethyl)-HCID 131735030N-Palmitoyl-Gly-His(Trt)-OtBu

Product 1

HCID 178443077HCID 178443077, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of TFA (206 ml), triisopropylsilane (10.8 ml), and H2O (10.8 ml) was added to N-palmitoyl-Gly-His(Trt)-OtBu (23.0 g, 30.8 mmol) while cooling with ice and the whole was stirred at room temperature for 1 hour. After concentration under reduced pressure, the residue was washed with diisopropyl ether and then diethyl ether, and then collected by filtration with a membrane-filter. The residue was reprecipitated with TFA (35 ml) and diethyl ether (800 ml), and the precipitate was dried under reduced pressure to give 16.2 g (93%) of a target compound.

Workup

  1. temperaturewhile cooling with ice
  2. concentrationAfter concentration under reduced pressure
  3. washthe residue was washed with diisopropyl ether
  4. filtrationdiethyl ether, and then collected by filtration with a membrane-filter
  5. customThe residue was reprecipitated with TFA (35 ml) and diethyl ether (800 ml)
  6. customthe precipitate was dried under reduced pressure

Sources & evidence

ORD record
ord-2d863e5948284bfea09b597a2a38a520
Source dataset
uspto-grants-2016_03
Patent number
US09289496B2

Reaction notes

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