Hydrochloric Acid → HCID 88173674, compound

HRID 2306082Notes

Reaction equation

HRID 2306082 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][C@@H:8]([OH:13])[CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.CCN=C=NCCC[N+](C)(C)C.[I-].ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.[CH2:47]([O:54][NH2:55])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.Cl>CN(C=O)C>[CH2:47]([O:54][NH:55][C:10](=[O:12])[CH2:9][C@H:8]([OH:13])[CH2:7][O:6][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:15][CH:14]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 102312Benzyloxyamine hydrochlorideHCID 1222421-(3-(Dimethylamino)propyl)-3-ethylcarbodiimide methiodideHCID 70145083HCID 70145083, compound

Product 1

HCID 88173674HCID 88173674, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 3C (121.2 g) in DMF (1 L) at 5° C. was treated sequentially with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide methiodide (92.9 g), 1-hydroxybenzotriazole (68.5 g), and 4-methylmorpholine (193 mL), stirred for 5 minutes, treated with O-benzylhydroxylamine hydrochloride (73.5 g), warmed to room temperature, treated with 5% HCl (2.1 L) over 35 minutes, and filtered. The solid was washed with water and dried under vacuum (100 mm Hg) at 50° C. with a nitrogen bleed to provide 156.9 g of the desired product. 1H NMR (300 MHz, DMSO-d6) δ11.05 (s, 1H), 7.45 (m, 2H), 7.35 (m, 5H), 6.90 (m, 2H), 5.21 (d, 1H, J=5 Hz), 4.80 (s, 2H), 4.20 (m, 1H), 3.88 (m, 2H), 2.25 (dd, 1H, 6, 14 Hz), 2.15 (dd, 1H, J=8,14 Hz).

Workup

  1. filtrationfiltered
  2. washThe solid was washed with water
  3. customdried under vacuum (100 mm Hg) at 50° C. with a nitrogen

Sources & evidence

ORD record
ord-e4f12bf5a72d447da4d5a374ccda0f20
Source dataset
uspto-grants-2002_08
Patent number
US06441189B1

Reaction notes

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