Trifluoroacetic acid → HCID 178449772, compound

HRID 1677621Notes

Reaction equation

HRID 1677621 reaction equation
C(OC([N:8]([C:19]1[CH:20]=[C:21]([CH:25]([O:29][P:30]([CH:33]([NH:37][C:38]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:39])[CH:34]([CH3:36])[CH3:35])([OH:32])=[O:31])[C:26]([OH:28])=[O:27])[CH:22]=[CH:23][CH:24]=1)[C:9]([NH2:18])=[N:10]C(OC(C)(C)C)=O)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]([C:19]1[CH:20]=[C:21]([CH:25]([O:29][P:30]([CH:33]([NH:37][C:38]([O:40][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[O:39])[CH:34]([CH3:35])[CH3:36])([OH:32])=[O:31])[C:26]([OH:28])=[O:27])[CH:22]=[CH:23][CH:24]=1)[C:9]([NH2:18])=[NH:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86629246HCID 86629246, compound

Product 1

HCID 178449772HCID 178449772, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-(N,N′-di(t-butoxycarbonyl)guanidino)phenyl)-2-((1-(benzyloxycarbonyl)amino-2-methylpropyl)(hydroxy)phosphinoyloxy)ethanoic acid in 10 mL of CH2Cl2 was added 5 mL of TFA. After stirring for 2 hours at ambient temperature, the solution was concentrated in vacuo and azeotrope with CH2Cl2 and MeOH. Purification by preparatory HPLC separated the two diastereomers and provided 72.9 mg (8%) of one diastereomer and 90.1 mg (10%) of 2-(3-guanidinophenyl)-2-((1-(benzyloxycarbonyl)amino-2-methylpropyl)(hydroxy)-phosphinoyloxy)ethanoic acid, NMR (DMSO-d6) 0.85 (m, 6), 2.05 (m, 1), 3.70 (m, 1), 4.80 (AB q, 2: doublets at 4.70, 4.90), 5.65 (d, 1), 7.20 (d, 1), 7.25-7.50 (m, 14), 9.85 (s, 1) ppm.

Workup

  1. concentrationthe solution was concentrated in vacuo and azeotrope with CH2Cl2 and MeOH
  2. customPurification by preparatory HPLC
  3. customseparated the two diastereomers

Sources & evidence

ORD record
ord-6079deb5113249e3a00a1cebcedbe1bb
Source dataset
uspto-grants-2011_08
Patent number
US08008325B2

Reaction notes

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