Methanesulfonyl chloride → HCID 86611758, compound

HRID 1716599Notes

Reaction equation

HRID 1716599 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]1[N:13]([C@@H:14]2[CH2:19][CH2:18][N:17]([CH2:20][C@@H:21]3[CH2:29][C:28]4[C:23](=[CH:24][CH:25]=[C:26]([NH:30][C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])[CH:27]=4)[CH2:22]3)[CH2:16][C@H:15]2[OH:36])[C:12]2[CH:37]=[CH:38][C:39]([CH3:41])=[CH:40][C:11]=2[N:10]=1.C(N(C(C)C)CC)(C)C.[CH3:51][S:52](Cl)(=[O:54])=[O:53].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:8][C:9]1[N:13]([CH:14]2[CH2:19][CH2:18][N:17]([CH2:20][C@H:21]3[CH2:29][C:28]4[C:23](=[CH:24][CH:25]=[C:26]([NH:30][C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])[CH:27]=4)[CH2:22]3)[CH2:16][CH:15]2[O:36][S:52]([CH3:51])(=[O:54])=[O:53])[C:12]2[CH:37]=[CH:38][C:39]([CH3:41])=[CH:40][C:11]=2[N:10]=1

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 86611759HCID 86611759, compound

Product 1

HCID 86611758HCID 86611758, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-{(S)-2-[(3R,4R)-4-(2,5-Dimethyl-benzoimidazol-1-yl)-3-hydroxy-piperidin-1-ylmethyl]-indan-5-yl}-isobutyramide; compound with trifluoro-acetic acid (235 mg; 0.51 mmol) and diisopropylethylamine (122 mL; 0.7 mmol) in CH2Cl2 was treated with methanesulfonyl chloride (47 mL; 0.6 mmol). The reaction mixture was stirred for 1 h and then poured into saturated NaHCO3. The aqueous phase was extracted three times with CH2Cl2 and the combined organic layers were dried over Na2SO4. Filtration and removal of volatiles under reduced pressure gave a brown solid from which the methanesulfonic acid 4-(2,5-dimethyl-benzoimidazol-1-yl)-1-((R)-5-isobutyrylamino-indan-2-ylmethyl)-piperidin-3-yl ester was isolated by flash chromatography (0-10% CH3OH in EtOAc) as a waxy solid (171 mg; 62%)

Workup

  1. extractionThe aqueous phase was extracted three times with CH2Cl2
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationFiltration and removal of volatiles under reduced pressure

Sources & evidence

ORD record
ord-e4134aff6dc34837b257d3ac22451467
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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