Triethylamine → tert-Butyl (1(S)-formyl-3(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-4-methylpentyl)carbamate

HRID 507829Notes

Reaction equation

HRID 507829 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:4][C@H:5]([CH2:9][NH:10][C:11](=[O:24])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:19][CH2:20][CH2:21][O:22][CH3:23])[CH:6]([CH3:8])[CH3:7].C(N(CC)CC)C>ClCCl.CS(C)=O>[CH:2]([C@@H:3]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:31])[CH3:30])[CH2:4][C@H:5]([CH2:9][NH:10][C:11](=[O:24])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:19][CH2:20][CH2:21][O:22][CH3:23])[CH:6]([CH3:7])[CH3:8])=[O:1]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 86613453tert-Butyl (1(S)-hydroxymethyl-3(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-4-methylpentyl)carbamate

Product 1

HCID 86613452tert-Butyl (1(S)-formyl-3(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-4-methylpentyl)carbamate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

The solution of 2.65 g of tert-butyl (1(S)-hydroxymethyl-3(S)-{[2-(3-methoxypropoxy)-benzoylamino]methyl}-4-methylpentyl)carbamate, 2.44 ml of triethylamine in 20 ml of dichloromethane is cooled to 0° C. The solution of 3.07 g of sulphur trioxide-pyridine complex in 12 ml of dimethyl sulphoxide is added dropwise over 1 hour and then the mixture is stirred for another 1 hour. The reaction mixture is admixed with 20 ml of ice-water and extracted with dichloromethane (3×). The combined organic phases are washed with 10% aqueous sodium hydrogensulphate solution, water, 1M sodium hydrogencarbonate solution and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a slightly yellowish foam. Rf=0.33 (3:1 EtOAc-heptane); Rt=4.65 (gradient I).

Workup

  1. extractionextracted with dichloromethane (3×)
  2. washThe combined organic phases are washed with 10% aqueous sodium hydrogensulphate solution, water, 1M sodium hydrogencarbonate solution and brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-689204c49b0c4057a82c613ccc1c67db
Source dataset
uspto-grants-2010_08
Patent number
US07786307B2

Reaction notes

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