Trifluoroacetic acid → HCID 178449992, compound

HRID 490952Notes

Reaction equation

HRID 490952 reaction equation
C(OC([N:8]=[C:9]([NH:40]C(OC(C)(C)C)=O)[NH:10][C:11]1[CH:12]=[C:13]([CH:17]([O:21][P:22]([C@@H:25]([NH:29][S:30]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)(=[O:32])=[O:31])[CH:26]([CH3:28])[CH3:27])([OH:24])=[O:23])[C:18]([OH:20])=[O:19])[CH:14]=[CH:15][CH:16]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:10]([C:11]1[CH:12]=[C:13]([CH:17]([O:21][P:22]([CH:25]([NH:29][S:30]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)(=[O:31])=[O:32])[CH:26]([CH3:28])[CH3:27])([OH:24])=[O:23])[C:18]([OH:20])=[O:19])[CH:14]=[CH:15][CH:16]=1)[C:9]([NH2:40])=[NH:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178448389HCID 178448389, compound

Product 1

HCID 178449992HCID 178449992, compoundYield 12.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-(N′,N″-di(t-butoxycarbonyl)guanidino)phenyl)-2-((1R)-(1-(benzylsulfonyl)amino-2-methylpropyl)(hydroxy)phosphinoyloxy)ethanoic acid (0.53 mmol) in 3 mL of methylene chloride was added TFA (3 mL, 39 mmol). After stirring for 1.5 hours at ambient temperature, the solution was concentrated. Purification by HPLC provided 33.0 mg (12%, 4 steps) of 2-(3-guanidinophenyl)-2-((1-(benzylsulfonyl)amino-2-methylpropyl)(hydroxy)phosphinoyloxy)ethanoic acid as white fluffy solid; NMR (DMSO-d6) 0.92 (m, 6), 2.01 (m, 1), 3.5 (m, 2), 4.54-4.26 (overlapping AB q, 2), 5.74 (overlapping doublets, 1), 7.22 (m, 1), 7.29-7.46 (m, 14), 9.78 (m, 1).

Workup

  1. concentrationthe solution was concentrated
  2. customPurification by HPLC

Sources & evidence

ORD record
ord-a841c250f92e4a879a4f3d0b53b11de5
Source dataset
uspto-grants-2009_05
Patent number
US07528173B2

Reaction notes

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