Sodium hydride → HCID 10573508, compound

HRID 1069574Notes

Reaction equation

HRID 1069574 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([CH3:18])=[C:5]2[CH2:19][C:20]([NH2:22])=[O:21].[H-].[Na+].[CH3:25][O:26][C:27](=[O:33])[CH2:28][CH2:29][CH2:30][CH2:31]Br>CS(C)=O>[CH3:25][O:26][C:27](=[O:33])[CH2:28][CH2:29][CH2:30][CH2:31][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([CH3:18])=[C:5]2[CH2:19][C:20]([NH2:22])=[O:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79557Methyl 5-bromovalerateHCID 10589888HCID 10589888, compound

Product 1

HCID 10573508HCID 10573508, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

As described in Example 23, 125 mg (0.43 mmol) of 5-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide (Example 2), 30 mg of 60% NaH/mineral oil, and 0.1 mL of 5-bromopentanoic acid methyl ester in 15 mL of DMSO were reacted to give 80 mg of 5-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]pentanoic acid methyl ester, after chromatography on silica (eluted with CH2Cl2→2% MeOH/CH2Cl2). This material in 5 mL of THF and 15 mL of EtOH was treated with 2 mL of 2N NaOH and the mixture stirred for 18 hours. After acidifying with 5N HCl, the mixture was extracted with EtOAc, the EtOAc solution washed with saturated NaCl solution, dried (Na2SO4), and concentrated at reduced pressure. The residue was dissolved in MeOH/CH2Cl2, concentrated and diluted with ether to give 80 mg (100% yield) of 5-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]pentanoic acid, mp, 168-169° C.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-84ebd7d277ae4384916a67e91d6fac4e
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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