1-Hydroxybenzotriazole → HCID 53941834, compound

HRID 1603066Notes

Reaction equation

HRID 1603066 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]([CH3:26])([CH3:25])[C:22](O)=[O:23])[CH:19]=2)[NH:14][C:13]=1[C:27]1[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[CH:28]=1)[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:36]1[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl.C12NC(CC1)CC2>C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C@H:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]([CH3:26])([CH3:25])[C:22]([N:36]3[CH:43]4[CH2:44][CH2:39][CH:40]3[CH2:41][CH2:42]4)=[O:23])[CH:19]=2)[NH:14][C:13]=1[C:27]1[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[CH:28]=1)[CH3:11])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15523808HCID 15523808, compoundHCID 162795037-Azabicyclo[2.2.1]heptane hydrochloride

Product 1

HCID 53941834HCID 53941834, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of (S)-2-[3-(2-tert-butoxycarbonylamino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid (2.5 g in 25 mL dry methylene chloride) at 0° C. was added 1-hydroxybenzotriazole (1.0 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.24 g) and the reagents allowed to mix for 1 hour. At this time a solution of 7-aza-bicyclo[2.2.1]heptane hydrochloride (1.44 g) was added followed by 1.5 mL triethylamine and the reaction stirred at room temperature. After 21 hours, the mixture was concentrated in vacuo and purified by flash chromatography on silica gel (hexane:ethyl acetate, 1:1) to give the title compound (2.6 g).

Workup

  1. additionto mix for 1 hour
  2. concentrationthe mixture was concentrated in vacuo
  3. custompurified by flash chromatography on silica gel (hexane:ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-5aa0bbc6926b4ebba3e77c35d17a91e9
Source dataset
uspto-grants-1999_11
Patent number
US05985901

Reaction notes

Loading…