Tert-Butylamine → HCID 69853956, compound

HRID 987926Notes

Reaction equation

HRID 987926 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]([CH2:20][CH:21]2[CH:26]([C:27](O)=[O:28])[CH2:25][CH:24]=[CH:23][CH2:22]2)[O:10][C:9]1([CH3:31])[CH3:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[C:53]([NH2:57])([CH3:56])([CH3:55])[CH3:54]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:11]([CH2:20][CH:21]2[CH:26]([C:27](=[O:28])[NH:57][C:53]([CH3:56])([CH3:55])[CH3:54])[CH2:25][CH:24]=[CH:23][CH2:22]2)[O:10][C:9]1([CH3:31])[CH3:30])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 69855094HCID 69855094, compound

Product 1

HCID 69853956HCID 69853956, compoundYield 9,512.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An ice-cooled, stirred solution of 4-benzyl-5-(6-carboxy-cyclohex-3-enylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (3.0 g) in dichloromethane (70 ml) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloide (1.61 g), 1-hydroxybenzotriazole and tert-butylamine (1.12 g). The reaction mixture was allowed to stir and warm to ambient temperature during 16 hours. The reaction mixture was then washed sequentially with 2M aqueous hydrochloric acid, 10% aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution, dried (anhydrous magnesium sulfate) and evaporated to give 4-benzyl-5-(6-tert-butylcarbamoyl-cyclohex-3-enylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (322 g, 95%)

Workup

  1. washThe reaction mixture was then washed sequentially with 2M aqueous hydrochloric acid, 10% aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution
  2. dry with materialdried (anhydrous magnesium sulfate)
  3. customevaporated

Sources & evidence

ORD record
ord-ed0e10ee7e7541ec9d6b2f0d040d8148
Source dataset
uspto-grants-2003_10
Patent number
US06632826B1

Reaction notes

Loading…