Hydrochloric Acid → HCID 9549260, compound

HRID 349508Notes

Reaction equation

HRID 349508 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH:30]([CH3:32])[CH3:31])[C:5](=[O:29])[C@@H:6]([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][S:14]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:27])[CH:23]=3)[CH:18]=2)(=[O:16])=[O:15])[C:9]1=[O:28])[CH3:7].N1C=CC=CC=1.[S:39](Cl)([CH3:42])(=[O:41])=[O:40].Cl>C(Cl)Cl>[Cl:27][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17]([S:14]([NH:13][C@H:10]1[CH2:11][CH2:12][N:8]([C@@H:6]([CH3:7])[C:5]([N:4]([CH:30]([CH3:32])[CH3:31])[CH2:3][CH2:2][NH:1][S:39]([CH3:42])(=[O:41])=[O:40])=[O:29])[C:9]1=[O:28])(=[O:15])=[O:16])[CH:26]=[CH:25]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 10311006HCID 10311006, compound

Product 1

HCID 9549260HCID 9549260, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(2S)-N-(2-Aminoethyl)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)-N-isopropylpropanamide (0.04 g) was dissolved in DCM (3 ml) at 0° C. and was treated with pyridine (0.027 ml) and mesyl chloride (0.03 ml). The reaction mixture was allowed to reach room temperature and then stirred at room temperature for 3 h. Additional DCM (3 ml) followed by hydrochloric acid (5 ml) was added. The organic layer was separated, dried (over magnesium sulphate) and concentrated under reduced pressure. The residue was purified using SPE (silica, eluting with DCM, diethyl ether, ethyl acetate:10% aqueous NH3) to give the title compound (0.024 g) as gum.

Workup

  1. customto reach room temperature
  2. additionwas added
  3. customThe organic layer was separated
  4. dry with materialdried (over magnesium sulphate)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified
  7. washSPE (silica, eluting with DCM, diethyl ether, ethyl acetate:10% aqueous NH3)

Sources & evidence

ORD record
ord-dce33710d8f349cc8edcd6ea84a32ed5
Source dataset
uspto-grants-2007_02
Patent number
US07179835B2

Reaction notes

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