Diisopropylethylamine → HCID 18459276, compound

HRID 2305014Notes

Reaction equation

HRID 2305014 reaction equation
[OH:1][C:2]([CH2:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)(=[O:25])=[O:24])([CH2:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)(=[O:9])=[O:8])[C:3](O)=[O:4].O.ON1C2C=CC=CC=2N=N1.Cl.[CH2:46]([O:53][NH2:54])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH2:46]([O:53][NH:54][C:3](=[O:4])[C:2]([OH:1])([CH2:22][S:23]([C:26]1[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=1)(=[O:25])=[O:24])[CH2:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)(=[O:9])=[O:8])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 102312Benzyloxyamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 18459324HCID 18459324, compound

Product 1

HCID 18459276HCID 18459276, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-hydroxy-2-[(4-methoxybenzenesulfonyl)methyl]-3-(4-phenylbenzenesulfonyl)propionic acid (0.6 g, 1.2 mmol) in 50 mL of methylene chloride is added 1-hydroxybenzotriazole monohydrate (0.185 g, 1.36 mmol), O-benzylhydroxylamine hydrochloride (0.218 g, 1.36 nmol), diisopropylethylamine (0.177 g, 1.36 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 0.262 g, 1.36 mmol), in that order. The clear, colorless solution is stirred overnight at ambient temperature. Methylene chloride is removed under reduced pressure and the residue is partitioned between ethyl acetate and water. The organic phase is washed with several portions of 1N HCl and then with aqueous potassium bicarbonate. It is dried over magnesium sulfate, filtered, concentrated, and chromatographed on silica gel. Elution with 1:1 ethyl acetate:hexanes affords the title compound as a white solid.

Workup

  1. customMethylene chloride is removed under reduced pressure
  2. customthe residue is partitioned between ethyl acetate and water
  3. washThe organic phase is washed with several portions of 1N HCl
  4. dry with materialIt is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed on silica gel
  8. washElution with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-a0cdf8b7086d414ba5a7d330d977e979
Source dataset
uspto-grants-2002_08
Patent number
US06437177B1

Reaction notes

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