Diethylamine → HCID 15523809, compound

HRID 322223Notes

Reaction equation

HRID 322223 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]([OH:24])=O)[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].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH2:57]([NH:59][CH2:60][CH3:61])[CH3:58]>C(Cl)Cl.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]([C:22](=[O:24])[N:59]([CH2:60][CH3:61])[CH2:57][CH3:58])([CH3:25])[CH3:26])[CH:19]=2)[NH:14][C:13]=1[C:27]1[CH:28]=[C:29]([CH3:34])[CH:30]=[C:31]([CH3:33])[CH:32]=1)[CH3:11])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15523808HCID 15523808, compound

Product 1

HCID 15523809HCID 15523809, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 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 in dry methylene chloride at 0° C. is added 1-hydroxybenzotriazole followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and the reagents allowed to mix for 1 hour. At this time diethylamine is added followed by 1.5 mL triehtylamine and the reaction stirred at room temperature. After completion, the mixture is concentrated in vacuo and purified by flash chromatography on silica gel to give the title compound.

Workup

  1. additionto mix for 1 hour
  2. concentrationAfter completion, the mixture is concentrated in vacuo
  3. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-f04d259459714356a2662e5c153ca7d6
Source dataset
uspto-grants-2001_04
Patent number
US06211224B1

Reaction notes

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