Methanesulfonyl chloride → HCID 67412114, compound

HRID 1949641Notes

Reaction equation

HRID 1949641 reaction equation
COC([N:5]1[CH2:9][CH:8]([C:10]2[C:18]3[C:13](=[CH:14][C:15]([F:19])=[CH:16][CH:17]=3)[NH:12][CH:11]=2)[CH:7]2[N:20]([C:23](=[O:39])[CH:24]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH2:21][CH2:22][CH:6]12)=O.CCN(C(C)C)C(C)C.[CH3:49][S:50](Cl)(=[O:52])=[O:51]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:35]([O:34][C:32](=[O:33])[NH:31][CH:24]([CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1)[C:23]([N:20]1[CH2:21][CH2:22][CH:6]2[N:5]([S:50]([CH3:49])(=[O:52])=[O:51])[CH2:9][CH:8]([C:10]3[C:18]4[C:13](=[CH:14][C:15]([F:19])=[CH:16][CH:17]=4)[NH:12][CH:11]=3)[CH:7]12)=[O:39])([CH3:38])([CH3:37])[CH3:36]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 674097574-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid methyl ester

Product 1

HCID 67412114HCID 67412114, compoundYield 49.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution containing 50 (200 mg, 0.41 mmol) and DIPEA (163 mg, 1.26 mmol) in anhydrous DCM (5 mL) was cooled to 0° C. A solution of MsCl (44 mg, 0.41 mmol) in DCM (0.5 mL) was added followed by the addition of DMAP (5 mg, cat.). After 2 h, the reaction mixture was diluted with DCM and washed successively with 1M HCl and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by flash silica gel chromatography (1:1 hexanes/EtOAc) to afford 114 mg (49%) of 61 as a white solid. Mass spectrum, m/z [563] (M+H)+.

Workup

  1. washwashed successively with 1M HCl and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by flash silica gel chromatography (1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-5c5f7ea2c620410da85a3707a53e7648
Source dataset
uspto-grants-2013_03
Patent number
US08399683B2

Reaction notes

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