Phosphonic acid → HCID 10815003, compound

HRID 1069609Notes

Reaction equation

HRID 1069609 reaction equation
P(=O)(O)O.C[O:6][P:7]([CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:19]([CH3:37])=[C:18]2[CH2:38][C:39]([NH2:41])=[O:40])(=[O:10])[O:8]C.C[Si](Br)(C)C.CO>C(Cl)Cl>[NH2:41][C:39](=[O:40])[CH2:38][C:18]1[C:17]2[C:21](=[CH:22][CH:23]=[C:15]([O:14][CH2:13][CH2:12][CH2:11][P:7](=[O:6])([OH:10])[OH:8])[CH:16]=2)[N:20]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:19]=1[CH3:37]

Participants

6

Reactant 4

HCID 407Phosphonic acidHCID 887MethanolHCID 76113BromotrimethylsilaneHCID 10768298HCID 10768298, compound

Product 1

HCID 10815003HCID 10815003, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[3-[[3-(2-Amino)-2-oxoethyl)-1-([1,1′-biphenyl]-2-ylmethyl)-2-methyl-1H-indol-5-yl]oxy]propyl]phosphonic acid. [3-[[3-(2-Amino-2-oxoethyl)-1-([1,1′-biphenyl]-2-ylmethyl)-2-methyl-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester (130 mg, 0.25 mmol) and 0.3 mL (3 mmol) of trimethylsilyl bromide in 2 mL of methylene chloride was stirred for 16 hours, 5 mL of MeOH added, stirred 0.75 hours and concentrated at reduced pressure. The residue was crystallized from EtOAc/MeCN/HOAc/water to give 41 mg (33% yield) of [3-[[3-(2-amino-2-oxoethyl)-1-([1,1′-biphenyl]-2-ylmethyl)-2-methyl-1H-indol-5-yl]oxy]propyl]phosphonic acid, mp, 200-202° C.

Workup

  1. concentrationconcentrated at reduced pressure
  2. customThe residue was crystallized from EtOAc/MeCN/HOAc/water

Sources & evidence

ORD record
ord-d93dcead6e4149609d38d547ac7491cd
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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