1,2-Dichloroethane → HCID 22881904, compound

HRID 1604220Notes

Reaction equation

HRID 1604220 reaction equation
[CH3:1][C:2]([CH3:16])([O:4][C:5]([NH:7][C@H:8]([C:13](O)=[O:14])[C:9]([SH:12])([CH3:11])[CH3:10])=[O:6])[CH3:3].O[N:18]1[C:22]2C=CC=CC=2N=N1.Cl.CN.CN1CCOCC1.C(Cl)CCl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH3:22][NH:18][C:13](=[O:14])[C@H:8]([C:9]([SH:12])([CH3:11])[CH3:10])[NH:7][C:5]([O:4][C:2]([CH3:16])([CH3:3])[CH3:1])=[O:6]

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 311Citric AcidHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 6364545Methylamine hydrochlorideHCID 14031165N-(tert-Butoxycarbonyl)-3-sulfanyl-L-valine

Product 1

HCID 22881904HCID 22881904, compoundYield 83.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of (R)-N-(1,1-dimethylethoxy)carbonylpenicillamine (14 g, 56.1 mmol), N-hydroxybenzotriazole (7.6 g, 56.1 mmol), methylamine hydrochloride (18.9 g, 280 mmol), N-methylmorpholine (34 ml, 308 mmol, 4-dimethylaminopyridine (685 mg, 5.6 mmol) and EDC (11.8 g, 62 mmol) in anhydrous dimethylformamide (300 ml) was stirred at RT overnight. The mixture was poured into 10% w/v citric acid (750 ml) and extracted with ether (3×500 ml). The combined extracts were then washed with 8% sodium bicarbonate (2×500 ml) and brine (500 ml), dried (MgSO4) and evaporated in vacuo to provide the title compound (12.3 g, 83%)

Workup

  1. extractionextracted with ether (3×500 ml)
  2. washThe combined extracts were then washed with 8% sodium bicarbonate (2×500 ml) and brine (500 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-a26be6b0dd9046a7a56257bdd958cf94
Source dataset
uspto-grants-1999_11
Patent number
US05994312

Reaction notes

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