Isovaleric Acid → HCID 69950083, compound

HRID 1956536Notes

Reaction equation

HRID 1956536 reaction equation
[C:1]([OH:7])(=O)[CH2:2][CH:3]([CH3:5])[CH3:4].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[C:30]([O:34][C:35](=[O:60])[NH:36][CH2:37][CH2:38][C:39]1[C:47]2[C:42](=[CH:43][CH:44]=[C:45]([C:48](=[NH:51])[NH:49]O)[CH:46]=2)[NH:41][C:40]=1[C:52]1[CH:57]=[C:56]([CH3:58])[CH:55]=[C:54]([CH3:59])[CH:53]=1)([CH3:33])([CH3:32])[CH3:31]>>[C:30]([O:34][C:35](=[O:60])[NH:36][CH2:37][CH2:38][C:39]1[C:47]2[C:42](=[CH:43][CH:44]=[C:45]([C:48]3[N:51]=[C:1]([CH2:2][CH:3]([CH3:5])[CH3:4])[O:7][N:49]=3)[CH:46]=2)[NH:41][C:40]=1[C:52]1[CH:53]=[C:54]([CH3:59])[CH:55]=[C:56]([CH3:58])[CH:57]=1)([CH3:33])([CH3:32])[CH3:31]

Participants

5

Reactant 4

HCID 10430Isovaleric AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178424873HCID 178424873, compound

Product 1

HCID 69950083HCID 69950083, compound

Procedure

To a stirred solution of isovaleric acid (0.025 mL in 4 mL methylene chloride) was added 1-hydroxybenzotriazole (37.8 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (43.6 mg) and the reagents allowed to mix for 30 minutes. At this time a solution of {2-[2-(3,5-dimethylphenyl)-5-(N-hydroxycarbamimidoyl)-1H-indol-3-yl]ethyl}carbamic acid tert-butyl ester (81 mg in 3 mL methylene chloride) was added and the reaction stirred at room temperature. After 2 hours, the mixture was concentrated in vacuo and purified by flash chromatography on silica gel (methylene chloride: methanol, 96:4) to give the title compound (81 mg).

Workup

  1. additionto mix for 30 minutes
  2. concentrationthe mixture was concentrated in vacuo
  3. custompurified by flash chromatography on silica gel (methylene chloride: methanol, 96:4)

Sources & evidence

ORD record
ord-5e32aa347e47491b9444d27036497e8a
Source dataset
uspto-grants-1998_07
Patent number
US05780437

Reaction notes

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