Trifluoroacetic acid → N-{2-[(3S)-3-amino-4-{[tert-butyl(diphenyl)silyl]oxy}butyl]phenyl}-Nalpha-(methoxycarbonyl)-beta-phenyl-L-phenylalaninamide

HRID 714130

Reaction equation

HRID 714130 reaction equation
[CH3:1][O:2][C:3](=[O:58])[NH:4][C@@H:5]([CH:45]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][C@H:17]([NH:37]C(OC(C)(C)C)=O)[CH2:18][O:19][Si:20]([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:7].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:37][C@H:17]([CH2:18][O:19][Si:20]([C:33]([CH3:36])([CH3:35])[CH3:34])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:16][CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH:8][C:6](=[O:7])[C@H:5]([CH:45]([C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[NH:4][C:3]([O:2][CH3:1])=[O:58]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68029329methyl[(2S)-1-({2-[(3S)-3-[(tert-butoxycarbonyl)amino]-4-{[tert-butyl(diphenyl)silyl]oxy}butyl]phenyl}amino)-1-oxo-3,3-diphenylpropan-2-yl]carbamate

Product 1

HCID 68029330N-{2-[(3S)-3-amino-4-{[tert-butyl(diphenyl)silyl]oxy}butyl]phenyl}-Nalpha-(methoxycarbonyl)-beta-phenyl-L-phenylalaninamideYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound methyl[(2S)-1-({2-[(3S)-3-[(tert-butoxycarbonyl)amino]-4-{[tert-butyl(diphenyl)silyl]oxy}butyl]phenyl}amino)-1-oxo-3,3-diphenylpropan-2-yl]carbamate (7, 305.4 mg, 0.382 mmol) was dissolved in a cold mixture of DCM (3 ml) and TFA (1 mL, 12.98 mmol) and the final solution stirred at 0° C. for 1.5 h, quenched at 0° C. by slow addition of saturated NaHCO3, then diluted with DCM, washed with saturated NaHCO3, dried over MgSO4, filtered and concentrated to afford 255 mg (95% yield) of the title compound as white foam submitted to the next step without further purification. MS: m/z=700.3 (MH+).

Workup

  1. customquenched at 0° C. by slow addition of saturated NaHCO3
  2. additiondiluted with DCM
  3. washwashed with saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3611c099fa244568bbe91520b1ecf4b6
Source dataset
uspto-grants-2015_11
Patent number
US09187415B2

Linked notes

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