Stannous chloride dihydrate → HCID 131724625, compound

HRID 393443Notes

Reaction equation

HRID 393443 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:15]([NH:17][C@H:18]([C:29]([OH:31])=[O:30])[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([N+]([O-])=O)=[CH:22][CH:21]=3)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.O.O.Cl[Sn]Cl>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2([C:15]([NH:17][C@H:18]([C:29]([OH:31])=[O:30])[CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 53735446HCID 53735446, compound

Product 1

HCID 131724625HCID 131724625, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 20 mL scintillation vial was added Wang resin linked N-[[1-(4-methoxyphenyl)cyclohexyl]carbonyl]-4-nitro-L-phenylalanine (241 mg, 0.14 mmol) prepared in Example 140 and 2 mL of a solution of 2M SnCl2.2H2O in DMF. The reaction mixture was shaken overnight at room temperature. The resulting resin was collected by filtration and was washed with DMF, isopropyl alcohol, dichloromethane, and ether to yield 243 mg (0.14 mmol) of 4-amino-N-[[(1-(4-methoxyphenyl)cyclohexyl]carbonyl]-L-phenylalanine on Wang resin.

Workup

  1. additionIn a 20 mL scintillation vial was added Wang resin
  2. filtrationThe resulting resin was collected by filtration
  3. washwas washed with DMF, isopropyl alcohol, dichloromethane, and ether

Sources & evidence

ORD record
ord-24b6552cd3074dcc937b893459bcb904
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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