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Toluene → HCID 178477537, compound

HRID 538365
Notes
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Reaction equation

HRID 538365 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20][C:21]1[N:26]=[C:25]([C@@:27](O)([CH3:42])[CH2:28][NH:29][S:30]([C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[C:24]([F:44])=[C:23]([Si:45]([CH2:50][CH3:51])([CH2:48][CH3:49])[CH2:46][CH3:47])[CH:22]=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>C1COCC1>[Br:20][C:21]1[N:26]=[C:25]([C:27]2([CH3:42])[CH2:28][N@@:29]2[S:30]([C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[C:24]([F:44])=[C:23]([Si:45]([CH2:50][CH3:51])([CH2:48][CH3:49])[CH2:46][CH3:47])[CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86668073(R)-N-(2-(6-bromo-3-fluoro-4-(triethylsilyl)pyridin-2-yl)-2-hydroxypropyl)-4-nitrobenzenesulfonamide

Product 1

HCID 178477537HCID 178477537, compoundYield 79.8%

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent

Procedure

A solution of triphenylphosphine (21.55 g, 82 mmol) and (R)—N-(2-(6-bromo-3-fluoro-4-(triethylsilyl)pyridin-2-yl)-2-hydroxypropyl)-4-nitrobenzenesulfonamide (37.56 g, 69 mmol) in 510 ml THF was cooled to 4° C. A solution of diethyl azodicarboxylate in toluene (40% by weight, 38.8 g, 89 mmol) was added in a dropwise while maintaining the temperature below 10° C. The cooling bath was removed and the rm was stirred at rt for 1 h. The reaction mixture was diluted with approx. 1000 ml toluene and THF was removed by evaporation at the rotavap. The resulting toluene solution of crude product was pre-purified on a silca gel column by eluting with hexanes/5-17% EtOAc. Purest fractions were combined, evaporated and crystallized from TBME/hexane to yield 29.2 g of the title compound as white crystals.

Workup

  1. temperaturewhile maintaining the temperature below 10° C
  2. customThe cooling bath was removed
  3. additionThe reaction mixture was diluted with approx. 1000 ml toluene and THF
  4. customwas removed by evaporation at the rotavap
  5. customThe resulting toluene solution of crude product was pre-purified on a silca gel column
  6. washby eluting with hexanes/5-17% EtOAc
  7. customevaporated
  8. customcrystallized from TBME/hexane

Sources & evidence

ORD record
ord-163af5c3ac0849e5b3412033437c826f
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08865712B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes