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Diisopropylethylamine → (R)-4-(4-morpholino-4-oxo-1-(phenylthio)butan-2-ylamino)-3-nitrobenzenesulfonamide

HRID 1771203
Notes
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Reaction equation

HRID 1771203 reaction equation
[NH2:1][C@@H:2]([CH2:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][C:4]([N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)=[O:5].CCN(C(C)C)C(C)C.F[C:30]1[CH:35]=[CH:34][C:33]([S:36]([NH2:39])(=[O:38])=[O:37])=[CH:32][C:31]=1[N+:40]([O-:42])=[O:41]>CN(C=O)C.CCOC(C)=O>[O:9]1[CH2:10][CH2:11][N:6]([C:4](=[O:5])[CH2:3][C@@H:2]([NH:1][C:30]2[CH:35]=[CH:34][C:33]([S:36]([NH2:39])(=[O:38])=[O:37])=[CH:32][C:31]=2[N+:40]([O-:42])=[O:41])[CH2:12][S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7][CH2:8]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 167824874-Fluoro-3-nitrobenzenesulfonamide2×HCID 59186675(R)-3-amino-1-morpholino-4-(phenylthio)butan-1-one2×

Product 1

HCID 11591105(R)-4-(4-morpholino-4-oxo-1-(phenylthio)butan-2-ylamino)-3-nitrobenzenesulfonamideYield 83%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (R)-3-amino-1-morpholino-4-(phenylthio)butan-1-one (INTERMEDIATE 72, 375.5 mg, 1.34 mmol) in DMF (2.5 ml) and DIPEA (1.20 Ml, 6.87 mmol) was added 4-fluoro-3-nitrobenzenesulfonamide (INTERMEDIATE 18, 325.8 mg, 1.48 mmol), and the resulting dark solution was stirred at 50° C. overnight, under a nitrogen atmosphere. The mixture was diluted with EtOAc (50 ml) and washed with water and brine (30 ml each), dried (Na2SO4), filtered, and evaporated under reduced pressure. The concentrate was purified by column chromatography (ISCO, 40 g silica gel column, eluting with 0→100% EtOAc/DCM) to give the title product (532.5 mg, yield: 83%).

Workup

  1. washwashed with water and brine (30 ml each)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe concentrate was purified by column chromatography (ISCO, 40 g silica gel column, eluting with 0→100% EtOAc/DCM)

Sources & evidence

ORD record
ord-8037d39dcccb434fb581492d4188ca24
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09248140B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes