Nitrogen → (S)-3-[3-(5-Bromo-2-dimethylcarbamoylsulfanyl-3-nitro-benzyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester

HRID 1747487Notes

Reaction equation

HRID 1747487 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([S:11][C:12](=[O:16])[N:13]([CH3:15])[CH3:14])=[C:4]([CH2:17]O)[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:38]([O:40][C:41](=[O:57])[CH2:42][C@@H:43]([N:47]1[C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][C:50]=2[NH:49][C:48]1=[O:56])[CH2:44][CH2:45][CH3:46])[CH3:39].N#N.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:38]([O:40][C:41](=[O:57])[CH2:42][C@@H:43]([N:47]1[C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][C:50]=2[N:49]([CH2:17][C:4]2[CH:3]=[C:2]([Br:1])[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]=2[S:11][C:12](=[O:16])[N:13]([CH3:14])[CH3:15])[C:48]1=[O:56])[CH2:44][CH2:45][CH3:46])[CH3:39]

Participants

7

Reactant 5

HCID 947NitrogenHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 59497467(S)-3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl esterHCID 59497682Dimethyl-thiocarbamic acid S-(4-bromo-2-hydroxymethyl-6-nitro-phenyl)ester

Product 1

HCID 59497582(S)-3-[3-(5-Bromo-2-dimethylcarbamoylsulfanyl-3-nitro-benzyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl esterYield 37.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dimethyl-thiocarbamic acid S-(4-bromo-2-hydroxymethyl-6-nitro-phenyl) ester (250 mg, 0.74 mmol), triphenylphosphine (215 mg, 0.82 mmol) and (S)-3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl ester (303 mg, 0.82 mmol,) are added to a flask with a N2 line. Dry THF (6 mL) is added and the reaction is cooled to 0° C. DIAD (1 ml of THF, 0.82 mmol) is added dropwise over the course of 5 minutes to the reaction and the reaction is warmed slowly to room temperature. The reaction is stirred for 1 hour then evaporated in vacuo and directly purified on silica gel with dichloromethane methanol as the eluent. Reaction is re-purified via-preparative LC/MS to give 166 mg (37%) of the desired compound. LCMS (ESMS): m/z 594.4 (M+H+).

Workup

  1. temperaturethe reaction is warmed slowly to room temperature
  2. customthen evaporated in vacuo
  3. customdirectly purified on silica gel with dichloromethane methanol as the eluent
  4. customReaction
  5. customis re-purified via-preparative LC/MS

Sources & evidence

ORD record
ord-edbd7430bcbd4b40ab1d657aa90fe941
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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