HCID 12044226, compound → HCID 53816025, compound

HRID 1976965Notes

Reaction equation

HRID 1976965 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=1)[NH:5][C:6]([C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:15])=[O:7].Cl[Sn]Cl.O>C(O)C>[CH3:1][O:2][C:3](=[O:26])[C@H:4]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([NH2:23])=[CH:21][CH:22]=1)[NH:5][C:6](=[O:7])[C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:15]

Participants

4

Reactant 2

HCID 12044226HCID 12044226, compoundHCID 43835034Tin dichloride dihydrate

Product 1

HCID 53816025HCID 53816025, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
97 °C

Procedure

N-[(2-Chloro-6-methylphenyl)carbonyl]-4-nitro-L-phenylalanine methyl ester (1.51 g, 4.0 mmol) and SnCl2.H2O (4.5 g, 20 mmol) were suspended in 30 mL of ethanol. The suspension was stirred at a bath temperature of 97° C. for 1 hr. After it was cooled to room temperature, the solvent was evaporated and the residue was dissolved in 15 mL of water. The aqueous solution was then made alkaline by addition of solid K2CO3 to pH>10 and was extracted with ethyl acetate (3×100 mL). The combined extracts were dried over K2CO3 and were concentrated to give 4-amino-N-(2-chloro-6-methylbenzoyl)-L-phenylalanine methyl ester as a light yellow foam (1.37 g).

Workup

  1. temperatureAfter it was cooled to room temperature
  2. customthe solvent was evaporated
  3. dissolutionthe residue was dissolved in 15 mL of water
  4. additionby addition of solid K2CO3 to pH>10
  5. extractionwas extracted with ethyl acetate (3×100 mL)
  6. dry with materialThe combined extracts were dried over K2CO3
  7. concentrationwere concentrated

Sources & evidence

ORD record
ord-a751df257e62473f9945f29c92901b35
Source dataset
uspto-grants-2001_05
Patent number
US06229011B1

Reaction notes

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