1-Hydroxybenzotriazole → HCID 53941834, compound

HRID 850671Notes

Reaction equation

HRID 850671 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 triehtylamine 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-6c0deb454188457a93fe39d00e973789
Source dataset
uspto-grants-2000_01
Patent number
US06017944

Reaction notes

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