Lithium Hydroxide → HCID 178449993, compound

HRID 490949Notes

Reaction equation

HRID 490949 reaction equation
C(OC([N:8]=[C:9]([NH:42]C(OC(C)(C)C)=O)[NH:10][C:11]1[CH:12]=[C:13]([CH:17]([O:22][P:23]([CH:26]([NH:30][S:31]([CH:34]=[CH:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)(=[O:33])=[O:32])[CH:27]([CH3:29])[CH3:28])([OH:25])=[O:24])[C:18]([O:20]C)=[O:19])[CH:14]=[CH:15][CH:16]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.[Li+].[OH-]>C(Cl)Cl.CO.O>[NH:10]([C:11]1[CH:12]=[C:13]([CH:17]([O:22][P:23]([CH:26]([NH:30][S:31]([CH:34]=[CH:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)(=[O:32])=[O:33])[CH:27]([CH3:29])[CH3:28])([OH:25])=[O:24])[C:18]([OH:20])=[O:19])[CH:14]=[CH:15][CH:16]=1)[C:9]([NH2:42])=[NH:8]

Participants

7

Reactant 3

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 178501876HCID 178501876, compound

Product 1

HCID 178449993HCID 178449993, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-(N′,N″-di(t-butoxycarbonyl)guanidino)phenyl)-2-((1-(2-phenylethenylsulfonyl)amino-2-methylpropyl)(hydroxy)-phosphinoyloxy)ethanoic acid, methyl ester (220 mg) in 5 mL methylene chloride was added 1 mL TFA. The reaction mixture was stirred at ambient temperature for 4 hours, then concentrated in vacuo to get an oil. The oil was dissolved in 2.5 mL MeOH, then a solution of LiOH (100 mg) in 3 mL water was added. The reaction mixture was stirred at ambient temperature for 2 hours. The crude product was purified by HPLC directly without work up to afford 2-(3-guanidinophenyl)-2-((1-(2-phenyl-ethenylsulfonyl)amino-2-methylpropyl)-(hydroxy)phosphinoyloxy)ethanoic acid, as a white solid (55 mg) NMR (DMSO-d6) 0.88 (m,6), 2.10 (m,1), 3.40 (m,1), 5.63 (m, 1), 7.10-7.60 (m, 11), 9.80 (d, 1) ppm.

Workup

  1. concentrationconcentrated in vacuo
  2. customto get an oil
  3. stirringThe reaction mixture was stirred at ambient temperature for 2 hours
  4. customThe crude product was purified by HPLC directly without work up

Sources & evidence

ORD record
ord-70d8688ee4f84768ada0d60022790fbd
Source dataset
uspto-grants-2009_05
Patent number
US07528173B2

Reaction notes

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