Hydrochloric Acid → HCID 22271933, compound

HRID 488648Notes

Reaction equation

HRID 488648 reaction equation
[CH3:1][Si:2]([CH3:27])([CH3:26])[CH2:3][CH2:4][O:5][C:6](=[O:25])[CH:7]([NH:20][C:21]([O:23][CH3:24])=[O:22])[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([NH2:19])=[CH:11][CH:10]=1.C1C=CC([I+][C:35]2[C:40]([C:41]([O-:43])=[O:42])=[CH:39][CH:38]=[CH:37][CH:36]=2)=CC=1.Cl>CN(C)C=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:24][O:23][C:21]([NH:20][CH:7]([C:6]([O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:26])[CH3:27])=[O:25])[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([NH:19][C:39]2[CH:38]=[CH:37][CH:36]=[CH:35][C:40]=2[C:41]([OH:43])=[O:42])=[CH:11][CH:10]=1)=[O:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 73883Iodonium, (2-carboxyphenyl)phenyl-, inner saltHCID 69804290HCID 69804290, compound

Product 1

HCID 22271933HCID 22271933, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(4-amino-naphthalen-1-yl)-2-methoxycarbonylamino-propionic acid 2-trimethylsilanyl-ethyl ester (0.93 g, 2.40 mmol), diphenyliodonium-2-carboxylate (1.22 g, 3.8 mmol, 1.5 eq) and copper(II) acetate (25 mg, 0.14 mmol, 0.06 eq) in N,N-dimethylformamide (25 mL) was heated to 100° C. for 14 hours, then cooled to room temperature. The mixture was acidified to a pH <3 with 1N HCl, extracted with ethyl acetate (3×35 mL). The combined organic layers were washed with 1N HCl (1×25 mL), water (1×25 mL), brine (1×25 mL), and dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified on silica gel eluting with 4:1 toluene/ethyl acetate to provide the titled compound. MS ESI(−)) m/e 507 (M−H)−.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate (3×35 mL)
  3. washThe combined organic layers were washed with 1N HCl (1×25 mL), water (1×25 mL), brine (1×25 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified on silica gel eluting with 4:1 toluene/ethyl acetate

Sources & evidence

ORD record
ord-05af6cacae5244798086cd5bfb8abd36
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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