Water → HCID 12042582, compound

HRID 2230182Notes

Reaction equation

HRID 2230182 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][O:15][CH3:16])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[S:7].[Cl-].[NH4+].O>CO.[Zn]>[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][O:15][CH3:16])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[S:7]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 12019596HCID 12019596, compound

Product 1

HCID 12042582HCID 12042582, compoundYield 106.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a suspension of N-[[1-(2-methoxyethyl)cyclopentyl]thioxomethyl]-4-nitro-L-phenylalanine methyl ester (4.58 g, 11.6 mmol), zinc dust (7.50 g, 116 mmol) and ammonium chloride (9.20 g, 174 mmol) in methanol (200 mL) was added H2O (100 mL) slowly over 5 min. After stirring for 20 min, the reaction mixture was partitioned between ethyl acetate (400 mL) and sat. ammonium chloride solution (150 mL). The separated aqueous layer was back-extracted with ethyl acetate (3×100 mL) and the organic layers were combined, dried over Na2SO4, filtered and concentrated in vacuo. The residual oil was dried under high vacuum for 2 h to give crude 4-amino-N-[[1-(2-methoxyethyl)cyclopentyl]thioxomethyl]-L-phenylalanine methyl ester (4.5 g).

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate (400 mL) and sat. ammonium chloride solution (150 mL)
  2. extractionThe separated aqueous layer was back-extracted with ethyl acetate (3×100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residual oil was dried under high vacuum for 2 h

Sources & evidence

ORD record
ord-7c2f65749ee24703a5cf1d048cf1f309
Source dataset
uspto-grants-2002_07
Patent number
US06423728B1

Reaction notes

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