Triphenylphosphine → HCID 66847985, compound

HRID 2060796Notes

Reaction equation

HRID 2060796 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2([NH:17][C:18]([NH:20][C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[S:19])[CH2:13][CH:12]([OH:14])[CH2:11][CH:10]2[CH2:15]O)[CH:5]=[CH:6][C:7]=1[F:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:9]23[CH2:13][CH:12]([OH:14])[CH2:11][CH:10]2[CH2:15][S:19][C:18]([NH:20][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:17]3)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 76656263HCID 76656263, compound

Product 1

HCID 66847985HCID 66847985, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of racemic N-((1SR,2RS,4RS)-1-(3-bromo-4-fluorophenyl)-4-hydroxy-2-(hydroxymethyl)cyclopentylcarbamothioyl)benzamide (1.21 g, 2.02 mmol) and triphenylphosphine (0.690 mg, 2.63 mmol) in anhydrous THF (18 mL) is added to a separate solution of di-tert-butyl azodicarboxylate (0.606 g, 2.63 mmol) in THF (36 mL) at room temperature. The reaction mixture is stirred at room temperature for 1 hr and concentrated under reduced pressure to give a residue that is purified by silica gel chromatography eluting with a linear gradient of 0% to 40% ethyl acetate in dichloromethane over 15 minutes to give the title compound as racemic mixture (0.557 g, 61%). ES/MS m/e (79Br/81Br) 449, 451 (M+1).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give a residue that
  3. customis purified by silica gel chromatography
  4. washeluting with a linear gradient of 0% to 40% ethyl acetate in dichloromethane over 15 minutes

Sources & evidence

ORD record
ord-914b12cb09a34697834bf8db76ba292c
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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