Triethylamine → HCID 178501872, compound

HRID 490950Notes

Reaction equation

HRID 490950 reaction equation
[CH2:1]([S:8](Cl)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][O:13][C:14](=[O:49])[CH:15]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][C:32]([NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=[N:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH:26]=1)[O:16][P:17]([C@@H:20]([NH2:24])[CH:21]([CH3:23])[CH3:22])([OH:19])=[O:18].C(N(CC)CC)C>C(Cl)Cl>[CH3:12][O:13][C:14](=[O:49])[CH:15]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][C:32]([NH:41][C:42]([O:44][C:45]([CH3:46])([CH3:48])[CH3:47])=[O:43])=[N:33][C:34]([O:36][C:37]([CH3:39])([CH3:40])[CH3:38])=[O:35])[CH:26]=1)[O:16][P:17]([C@@H:20]([NH:24][S:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:10])=[O:9])[CH:21]([CH3:23])[CH3:22])([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74740Phenylmethanesulfonyl chlorideHCID 178501870HCID 178501870, compound

Product 1

HCID 178501872HCID 178501872, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Alternatively, to a solution of benzylsulfonyl chloride (101.4 mg, 0.53 mmol) and 2-(3-(N′,N″-di(t-butoxycarbonyl)guanidino)phenyl)-2-((1R)-(1-amino-2-methylpropyl)(hydroxy)-phosphinoyloxy)ethanoic acid methyl ester (301.4 mg, 0.54 mmol) in 4 mL of methylene chloride was added triethylamine (0.13 mL, 0.93 mmol). After stirring at ambient temperature for 1.5 hours, the reaction mixture was concentrated in vacuo to give a yellow oil, 2-(3-(N′,N″-di(t-butoxy-carbonyl)guanidino)phenyl)-2-((1R)-(1-(benzylsulfonyl)amino-2-methylpropyl)-(hydroxy)phosphinoyloxy)ethanoic acid methyl ester, which was used without further purification in the following step.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-869dd7175e254e62ad854db306411419
Source dataset
uspto-grants-2009_05
Patent number
US07528173B2

Reaction notes

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