Water → HCID 12042582, compound

HRID 990120Notes

Reaction equation

HRID 990120 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).The separated aqueous layer
  2. extractionwas 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-a31eb5adf7274b24bc85108c439eaaf9
Source dataset
uspto-grants-2002_10
Patent number
US06458844B2

Reaction notes

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