1-Hydroxybenzotriazole → HCID 66658532, compound

HRID 1951906Notes

Reaction equation

HRID 1951906 reaction equation
Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[CH2:23]([O:30][C:31]([NH:33][C:34]1([C:37]([OH:39])=O)[CH2:36][CH2:35]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[CH2:40]([NH:47][CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>ClCCl>[CH2:40]([N:47]([C:37]([C:34]1([NH:33][C:31]([O:30][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:32])[CH2:35][CH2:36]1)=[O:39])[CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 80908N-Benzylglycine ethyl esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 35890121-{[(Benzyloxy)carbonyl]amino}cyclopropane-1-carboxylic acid

Product 1

HCID 66658532HCID 66658532, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (21.0 g, 110 mmol) and 1-hydroxybenzotriazole (2.70 g, 20 mmol) were added to a dichloromethane (235 ml) solution of 1-{[(benzyloxy)carbonyl]amino}cyclopropanecarboxylic acid (23.5 g, 100 mmol) and ethyl N-benzylglycinate (19.3 g, 100 mmol) under ice cooling and the resulting mixture was stirred at room temperature for 24 hours. The solvent was concentrated under reduced pressure and then the residue was diluted with ethyl acetate, washed with 1 N aqueous hydrochloric acid solution, saturated aqueous sodium bicarbonate solution, and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography [n-hexane:ethyl acetate=2:1 (v/v)] to give the title compound (35.7 g, 87%) as a colorless solid.

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with 1 N aqueous hydrochloric acid solution, saturated aqueous sodium bicarbonate solution, and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography [n-hexane:ethyl acetate=2:1 (v/v)]

Sources & evidence

ORD record
ord-dbdc03530dc24ad38d436a7b283d51ea
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

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