Methanol → HCID 10766584, compound

HRID 2292802Notes

Reaction equation

HRID 2292802 reaction equation
NC(=O)CC1C2C(=CC=CC=2OCCCP(=O)(O)O)N(CC2C=CC=C(Cl)C=2)C=1CC.C[O:33][P:34]([CH2:38][CH2:39][CH2:40][O:41][C:42]1[CH:43]=[C:44]2[C:48](=[CH:49][CH:50]=1)[N:47]([CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[C:54]([Cl:58])[CH:53]=1)[C:46]([CH2:59][CH3:60])=[C:45]2[CH2:61][C:62]([NH2:64])=[O:63])(=[O:37])[O:35]C.C[Si](Br)(C)C.CO>C(Cl)Cl>[NH2:64][C:62](=[O:63])[CH2:61][C:45]1[C:44]2[C:48](=[CH:49][CH:50]=[C:42]([O:41][CH2:40][CH2:39][CH2:38][P:34](=[O:33])([OH:37])[OH:35])[CH:43]=2)[N:47]([CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[C:54]([Cl:58])[CH:53]=2)[C:46]=1[CH2:59][CH3:60]

Participants

6

Reactant 4

HCID 887MethanolHCID 76113BromotrimethylsilaneHCID 10815030HCID 10815030, compoundHCID 21191842HCID 21191842, 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-4-yl]oxy]propyl]phosphonic acid. [[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-435a72414f4d4ee08214dc3f1164e272
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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