Hydrochloric Acid → (3R)-4-Amino-3-(3-{[(3,4-dichlorophenyl)sulfonyl]amino}-4-chlorophenyl)butanoic acid

HRID 1799203

Reaction equation

HRID 1799203 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[CH2:13][NH:12][C:11](=[O:14])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(C(C)C)CC)(C)C.[Cl:24][C:25]1[CH:26]=[C:27]([S:32](Cl)(=[O:34])=[O:33])[CH:28]=[CH:29][C:30]=1[Cl:31].Cl.Cl.NC[C@@H](C1C=CC(Cl)=C(Br)C=1)CC(O)=[O:43]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[NH2:12][CH2:13][C@@H:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([NH:1][S:32]([C:27]2[CH:28]=[CH:29][C:30]([Cl:31])=[C:25]([Cl:24])[CH:26]=2)(=[O:34])=[O:33])[CH:3]=1)[CH2:10][C:11]([OH:14])=[O:43]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 81531DiisopropylethylamineHCID 66724932(4R)-4-(3-amino-4-chlorophenyl)pyrrolidin-2-oneHCID 66725034(3R)-4-amino-3-(3-bromo-4-chlorophenyl)butanoic acid hydrochloride

Product 1

HCID 49793116(3R)-4-Amino-3-(3-{[(3,4-dichlorophenyl)sulfonyl]amino}-4-chlorophenyl)butanoic acid

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

(4R)-4-(3-Amino-4-chlorophenyl)pyrrolidin-2-one (0.105 g, 0.5 mmol) was dissolved in 2 mL of methylene chloride (2 mL). Diisopropylethylamine (0.14 mL, 0.75 mmol) was added followed by 3,4-dichlorobenzenesulfonyl chloride (0.134 g, 0.55 mmol) and a catalytic amount of DMAP (0.05 mmol). The mixture was stirred overnight at room temperature. The mixture was then diluted with methylene chloride (50 mL), washed with water, then brine, and concentrated to give the product, which was treated with HCl as described for the preparation of (3R)-4-amino-3-(3-bromo-4-chlorophenyl)butanoic acid hydrochloride to provide the title compound (21). MS (ESI) m/z 438.89 (M+H)+.

Workup

  1. washwashed with water
  2. concentrationbrine, and concentrated
  3. customto give the product, which

Sources & evidence

ORD record
ord-b680394f819f43e796659c48df9f4f3a
Source dataset
uspto-grants-2013_01
Patent number
US08344028B2

Linked notes

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