Triethylamine → HCID 69597633, compound

HRID 1796811Notes

Reaction equation

HRID 1796811 reaction equation
[NH2:1][CH:2]([CH3:31])[CH:3]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:19][CH:18]=1)(=[O:16])=[O:15])[C:4]12[O:11][CH2:10][C:7]([CH3:12])([CH2:8][O:9]1)[CH2:6][O:5]2.C(N(CC)CC)C.Cl[C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41]>O1CCOCC1.O.C(OCC)(=O)C>[CH2:43]([O:42][C:40](=[O:41])[NH:1][CH:2]([CH3:31])[CH:3]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:19][CH:18]=1)(=[O:16])=[O:15])[C:4]12[O:5][CH2:6][C:7]([CH3:12])([CH2:10][O:11]1)[CH2:8][O:9]2)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 22182462HCID 22182462, compound

Product 1

HCID 69597633HCID 69597633, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

A solution of N-[2-amino-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-propyl]-4-benzyloxy-benzenesulfonamide (compound of formula LI, 2.5 g, 5.6 mmol), triethyl amine (1.01 ml, 0.73 g, 7.22 mmol) in 31 ml of 2:1 (v/v) 1,4-dioxane-water was treated with benzyl chloroformate (1.20 ml, 1.43 g, 8.40 mmol) at about 0° C. After stirring for about 3 hours at about 0° C., the mixture was diluted with ethyl acetate, washed twice with water, once with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 2:1 hexane-ethyl acetate, affording 2.0 g of [2-(4-benzyloxy-benzenesulfonylamino)-1-methyl-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-ethyl]-carbamic acid benzyl ester (compound of formula LII) as a colorless syrup.

Workup

  1. washwashed twice with water, once with brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 2:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-cc6ce70eac0b47c0b72c03e12959936b
Source dataset
uspto-grants-2006_04
Patent number
US07030242B2

Reaction notes

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