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Methanesulfonyl chloride → N-[1-(4-Methanesulfonyl-6-phenoxy-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl)-2-methyl-propyl]-2-methylamino-propionamide

HRID 1965166
Notes
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Reaction equation

HRID 1965166 reaction equation
C(O[C:9](=O)[N:10](C)[CH:11]([C:13](=[O:36])[NH:14][CH:15]([C:19]([N:21]1[CH2:25][CH2:24][CH:23]2[NH:26][CH2:27][CH:28]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:22]12)=[O:20])[CH:16]([CH3:18])[CH3:17])[CH3:12])C1C=CC=CC=1.CCN(C(C)C)C(C)C.[CH3:48][S:49](Cl)(=[O:51])=[O:50]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:48][S:49]([N:26]1[CH:23]2[CH:22]([N:21]([C:19]([CH:15]([NH:14][C:13](=[O:36])[CH:11]([NH:10][CH3:9])[CH3:12])[CH:16]([CH3:18])[CH3:17])=[O:20])[CH2:25][CH2:24]2)[CH:28]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:27]1)(=[O:51])=[O:50]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67608270Methyl-{1-[2-methyl-1-(6-phenoxy-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl)-propylcarbamoyl]-ethyl}-carbamic acid benzyl ester

Product 1

HCID 67517487N-[1-(4-Methanesulfonyl-6-phenoxy-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl)-2-methyl-propyl]-2-methylamino-propionamide

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution containing 18 (150 mg, 0.28 mmol) in DCM (3 mL) was cooled to 0° C. DIPEA (74 mg, 0.57 mmol) and DMAP (4 mg, 0.03 mmol) were added followed by the addition of MsCl (36 mg, 0.32 mmol). After 1 h, the reaction mixture was warmed to ambient temperature, diluted with DCM, washed successively with 1M HCl and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford the crude sulfonamide which was used without further purification. Mass spectrum, m/z [601] (M+H)+.

Workup

  1. temperaturethe reaction mixture was warmed to ambient temperature
  2. washwashed successively with 1M HCl and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a421510577d14b70bbde42bd02d89089
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08415486B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes