methyl (3S)-3-amino-3-(2-chlorophenyl)propanoate → HCID 178500728, compound

HRID 72364Notes

Reaction equation

HRID 72364 reaction equation
[CH3:1][C:2]1([CH3:22])[C:7]([CH3:9])([CH3:8])[O:6][C:5](OC2C=CC([N+]([O-])=O)=CC=2)=[N:4][S:3]1(=[O:21])=[O:20].[NH2:23][C@H:24]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[Cl:36])[CH2:25][C:26]([O:28][CH3:29])=[O:27]>ClCCl.C(N(CC)C(C)C)(C)C>[CH3:29][O:28][C:26](=[O:27])[CH2:25][C@@H:24]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[Cl:36])[NH:23][C:5]1[O:6][C:7]([CH3:8])([CH3:9])[C:2]([CH3:1])([CH3:22])[S:3](=[O:20])(=[O:21])[N:4]=1

Participants

5

Reactant 2

HCID 7131820methyl (3S)-3-amino-3-(2-chlorophenyl)propanoateHCID 718136815,5,6,6-Tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

Product 1

HCID 178500728HCID 178500728, compoundYield 77.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

200 mg of 5,5,6,6-tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide and 130 mg of methyl(S)-3-amino-3-(2-chlorophenyl)propionate were dissolved in 5 ml of dichloromethane and 0.52 ml of N,N-diisopropylethylamine, and the mixture was stirred at room temperature for 16 hours. Subsequently, the reaction solution was diluted with 20 ml of dichloromethane and washed repeatedly with 20 ml of 25% aqueous ammonia solution, until the organic phase was colorless. The organic phase was dried over Na2SO4 and concentrated by rotary evaporation. This gave the product (191 mg) with a molecular weight of 402.9 g/mol (C17H23ClN2O5S); MS (ESI): m/e=403 (M+H+).

Workup

  1. washwashed repeatedly with 20 ml of 25% aqueous ammonia solution, until the organic phase
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-c163ac537af7401d95c1557b16251adb
Source dataset
uspto-grants-2014_09
Patent number
US08828994B2

Reaction notes

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