Trifluoroacetic acid → tert-Butyl 4-((S)-2-amino-3-((R)-2-methyloxiran-2-yl)-3-oxopropyl)benzylcarbamate TFA salt

HRID 1912361Notes

Reaction equation

HRID 1912361 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C@H:17]([NH:24]C(=O)OCC2C=CC=CC=2)[C:18]([C@@:20]2([CH3:23])[CH2:22][O:21]2)=[O:19])=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>CO>[OH:41][C:35]([C:37]([F:40])([F:39])[F:38])=[O:36].[NH2:24][C@H:17]([C:18]([C@@:20]1([CH3:23])[CH2:22][O:21]1)=[O:19])[CH2:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71562239Benzyl ((S)-3-(4-((tert-butyloxycarbonylamino)methyl)phenyl)-1-((R)-2-methyloxiran-2-yl)-1-oxopropan-2-yl)carbamate

Product 1

HCID 71562240tert-Butyl 4-((S)-2-amino-3-((R)-2-methyloxiran-2-yl)-3-oxopropyl)benzylcarbamate TFA salt

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cbz-protected amine 14 (107 mg, 0.23 mmol) was dissolved in MeOH (5 mL) and to this was added TFA (1.2 eq., 0.27 mmol, 21 μL). Argon was bubbled through the solution for 15 minutes, after which Pd black (10 mg) was added and the flask was charged with hydrogen gas. After 10 minutes, TLC analysis indicated complete conversion of starting material and all solids were removed by filtration over CELITE. Toluene (10 mL) was added and the mixture was concentrated under reduced pressure followed by coevaporation with toluene (2×) in order to remove excess TFA. The purity of the deprotected amine (as TFA salt) was confirmed by LC-MS analysis and the compound was subjected to the next step without further purification.

Workup

  1. customArgon was bubbled through the solution for 15 minutes
  2. additionafter which Pd black (10 mg) was added
  3. additionthe flask was charged with hydrogen gas
  4. customall solids were removed by filtration over CELITE
  5. additionToluene (10 mL) was added
  6. concentrationthe mixture was concentrated under reduced pressure
  7. customto remove excess TFA
  8. customthe compound was subjected to the next step without further purification

Sources & evidence

ORD record
ord-ec0ea96e067a43929c2a3379e0c618e1
Source dataset
uspto-grants-2013_12
Patent number
US08609610B2

Reaction notes

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