Methanol → HCID 10766584, compound

HRID 1069622Notes

Reaction equation

HRID 1069622 reaction equation
C[O:2][P:3]([CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1)[C:15]([CH2:28][CH3:29])=[C:14]2[CH2:30][C:31]([NH2:33])=[O:32])(=[O:6])[O:4]C.C[Si](Br)(C)C.CO>C(Cl)Cl>[NH2:33][C:31](=[O:32])[CH2:30][C:14]1[C:13]2[C:17](=[CH:18][CH:19]=[C:11]([O:10][CH2:9][CH2:8][CH2:7][P:3](=[O:2])([OH:6])[OH:4])[CH:12]=2)[N:16]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)[C:15]=1[CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 887MethanolHCID 76113BromotrimethylsilaneHCID 10815030HCID 10815030, compound

Product 1

HCID 10766584HCID 10766584, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[[3-[[3-(2-Amino-2-oxoethyl)-1-[(3-chlorophenyl)methyl]-2-ethyl-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester (99 mg, 0.2 mmol) and 0.21 mL (1.6 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 60 mg (65% yield) of [3-[[3-(2-amino-2-oxoethyl)-1-[(3-chlorophenyl)methyl]-2-ethyl-1H-indol-5-yl]oxy]propyl]phosphonic acid, mp, 203-205° C.

Workup

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

Sources & evidence

ORD record
ord-9656e0cedc7b4071ab03c062eb26b9d8
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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