1-Hydroxybenzotriazole → HCID 53720126, compound

HRID 2108281Notes

Reaction equation

HRID 2108281 reaction equation
[C:1]([S:4][CH:5]([CH:10]([C:15]([NH:17][C@H:18]([C:28]([NH:30][CH3:31])=[O:29])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:6][C:7](O)=[O:8])(=[O:3])[CH3:2].ON1C2C=CC=CC=2N=N1.Cl.[NH2:43][CH2:44][C:45]([NH2:47])=[O:46].C(N(C(C)C)CC)(C)C>ClCCl>[C:1]([S:4][CH:5]([CH2:6][C:7]([NH:43][CH2:44][C:45]([NH2:47])=[O:46])=[O:8])[CH:10]([CH2:11][CH:12]([CH3:13])[CH3:14])[C:15]([NH:17][C@H:18]([C:28]([NH:30][CH3:31])=[O:29])[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)=[O:16])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2723639Glycinamide hydrochlorideHCID 18639816HCID 18639816, compound

Product 1

HCID 53720126HCID 53720126, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 3-acetylmercapto-6-methyl-4-[[[1-(S)-[(methylamino)carbonyl]-2-(4-methoxyphenyl)ethyl]amino]carbonyl]heptanoic acid (E5, Isomer A; 226 mg, 0.5 mmol), N-ethyl-N1 -dimethylaminopropylcarbodiimide hydrochloride (116 mg, 0.6 mmol), 1-hydroxybenzotriazole (90 mg, 0.58 mmol), glycinamide hydrochloride (64 mg, 0.58 mmol) and diisopropylethylamine (0.2 ml, 1.14 mmol) in dichloromethane was stirred at 5° C. for 2 h then at room temperature overnight. The mixture was cooled in ice and the solid was collected by filtration and washed well with dichloromethane. The solid was triturated with 1M citric acid, then filtered, washed with water and dried. Recrystallisation from methanol/ether gave the title compound as a single isomer (Isomer A), 75 mg (30%) mp 218°-219° C.

Workup

  1. customat room temperature
  2. customovernight
  3. temperatureThe mixture was cooled in ice
  4. filtrationthe solid was collected by filtration
  5. washwashed well with dichloromethane
  6. customThe solid was triturated with 1M citric acid
  7. filtrationfiltered
  8. washwashed with water
  9. customdried
  10. customRecrystallisation from methanol/ether

Sources & evidence

ORD record
ord-f75ae47ab3e142879cbf62352751f767
Source dataset
uspto-grants-1990_06
Patent number
US04937243

Reaction notes

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