Acetic Acid → 2-{3-[((S)-1-dimethylaminomethyl-2-phenyl-ethylamino)-methyl]-benzyl}-1,1-dioxo-1lambda6-isothiazolidine-3-carboxylic acid ethyl ester

HRID 1879467Notes

Reaction equation

HRID 1879467 reaction equation
[CH3:1][NH:2][CH2:3][C@@H:4]([NH:12][CH3:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:14]([O:16][C:17]([CH:19]1[CH2:23][CH2:22][S:21](=[O:25])(=[O:24])[N:20]1[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29](C=O)[CH:28]=1)=[O:18])[CH3:15].[C:35]([BH3-])#N.[Na+].C(O)(=O)C>CO.C(OCC)(=O)C>[CH2:14]([O:16][C:17]([CH:19]1[CH2:23][CH2:22][S:21](=[O:24])(=[O:25])[N:20]1[CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]([CH2:13][NH:12][C@H:4]([CH2:3][N:2]([CH3:35])[CH3:1])[CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:32]=1)=[O:18])[CH3:15]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 136896881,2-Propanediamine, N,N'-dimethyl-3-phenyl-, (S)-HCID 582804492-(3-Formyl-benzyl)-1,1-dioxo-1lambda6 isothiazolidine-3-carboxylic acid ethyl ester2×

Product 1

HCID 582804542-{3-[((S)-1-dimethylaminomethyl-2-phenyl-ethylamino)-methyl]-benzyl}-1,1-dioxo-1lambda6-isothiazolidine-3-carboxylic acid ethyl esterYield 112.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)—N,N′-dimethyl-3-phenyl-propane-1,2-diamine (120 mg, 0.673 mmol) in methanol (2 mL) under argon was added a solution of 2-(3-formyl-benzyl)-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid ethyl ester (Intermediate 4; 230.5 mg, 0.740 mmol) in methanol (4 mL). The solution was cooled 0° C. in an ice bath and to this was added sodium cyanoborohydride (63.4 mg, 1.01 mmol) and acetic acid (0.3 mL). The solution was allowed to warm to room temperature and stirred for 16 h under argon. The reaction mixture was diluted with ethyl acetate (50 mL), washed with water (2×10 mL) and the aqueous layer was extracted with ethyl acetate (50 mL). The combined organics were dried over sodium sulfate, filtered and concentrated to give crude 2-{3-[((S)-1-dimethylaminomethyl-2-phenyl-ethylamino)-methyl]-benzyl}-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid ethyl ester (360 mg) as colorless oil.

Workup

  1. temperatureto warm to room temperature
  2. washwashed with water (2×10 mL)
  3. extractionthe aqueous layer was extracted with ethyl acetate (50 mL)
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2c4629b4633547b198ad22ba001386cb
Source dataset
uspto-grants-2012_11
Patent number
US08314250B2

Reaction notes

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