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

HRID 1881457Notes

Reaction equation

HRID 1881457 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-fbf61c43b561452592c4a9865e1c0d68
Source dataset
uspto-grants-2012_11
Patent number
US08318767B2

Reaction notes

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