Methanesulfonyl chloride → HCID 58826456, compound

HRID 2244693Notes

Reaction equation

HRID 2244693 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([OH:10])[C@@H:7]([NH:11][C:12]([C:14]2[S:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:13])[CH2:6]1)=[O:4].C(N(C(C)C)C(C)C)C.[S:29](Cl)([CH3:32])(=[O:31])=[O:30]>C(Cl)Cl.O>[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([O:10][S:29]([CH3:32])(=[O:31])=[O:30])[C@@H:7]([NH:11][C:12]([C:14]2[S:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:13])[CH2:6]1)=[O:4]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58826453HCID 58826453, compound

Product 1

HCID 58826456HCID 58826456, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (1R,3S,4R)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-cyclopentane-carboxylic acid methyl ester (136 mg) in CH2Cl2 (5 ml) was treated at 0° C. with N-ethyl-diisopropyl amine (0.38 ml) and mesyl chloride (0.04 ml). The reaction mixture was stirred at 0° C., then diluted with H2O and extracted with CH2Cl2. The organic layer was washed with H2O, dried over MgSO4 and concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2→CH2Cl2MeOH 95:5) to give (1R,3S,4R)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-methanesulfonyloxy-cyclopentanecarboxylic acid methyl ester (159 mg) as off-white solid. MS 380.1 ([M−H]−).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with H2O
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (silica gel

Sources & evidence

ORD record
ord-ed3546055bab43beae5183c1a71db3e9
Source dataset
uspto-grants-2010_03
Patent number
US07678917B2

Reaction notes

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