1-Hydroxybenzotriazole → Benzyl {1-(4-bromobenzyl)-2-[(2-hydroxy-4,4-dimethylhexyl)amino]-2-oxoethyl}carbamate

HRID 425376Notes

Reaction equation

HRID 425376 reaction equation
C(=O)(O)[O-].[Na+].[CH2:6]([O:13][C:14]([NH:16][CH:17]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1)[C:18]([OH:20])=O)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH2:29][CH2:30][CH:31]([OH:38])[CH2:32][C:33]([CH3:37])([CH3:36])[CH2:34][CH3:35].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C(Cl)Cl>[Br:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][CH:17]([NH:16][C:14](=[O:15])[O:13][CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:18]([NH:29][CH2:30][CH:31]([OH:38])[CH2:32][C:33]([CH3:37])([CH3:36])[CH2:34][CH3:35])=[O:20])=[CH:23][CH:24]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220659152-{[(Benzyloxy)carbonyl]amino}-3-(4-bromophenyl)propanoic acidHCID 55289824HCID 55289824, compound

Product 1

HCID 86637795Benzyl {1-(4-bromobenzyl)-2-[(2-hydroxy-4,4-dimethylhexyl)amino]-2-oxoethyl}carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium bicarbonate (17.36 g, 207 mmol) was added to an ambient temperature solution of 2-{[(benzyloxy)carbonyl]amino}-3-(4-bromophenyl)propanoic acid (7.79 g, 20.7 mmol), 1-amino-4,4-dimethylhexan-2-ol (3 g, 20.7 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (7.92 g, 41.4 mmol) and 1-hydroxybenzotriazole (5.58 g, 41.4 mmol) in methylene chloride (150 mL). After stirring at ambient temperature overnight, the reaction mixture was quenched with water and extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-80% ethyl acetate/hexane afforded benzyl {1-(4-bromobenzyl)-2-[(2-hydroxy-4,4-dimethylhexyl)amino]-2-oxoethyl}carbamate.

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a0aaf2f18fe4fa38478c859eeb40dbe
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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