Sodium Thiosulfate → methyl 4-[(1S)-1-({[2,5-dichloro-4-(3-chlorobenzoyl)-3-thienyl]carbonyl}amino)ethyl]benzoate

HRID 870054Notes

Reaction equation

HRID 870054 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[S:25][C:26]([Cl:53])=[C:27]([CH:44]([C:46]2[CH:51]=[CH:50][CH:49]=[C:48]([Cl:52])[CH:47]=2)[OH:45])[C:28]=1[C:29]([NH:31][C@H:32]([C:34]1[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=1)[CH3:33])=[O:30].C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[Cl:23][C:24]1[S:25][C:26]([Cl:53])=[C:27]([C:44](=[O:45])[C:46]2[CH:51]=[CH:50][CH:49]=[C:48]([Cl:52])[CH:47]=2)[C:28]=1[C:29]([NH:31][C@H:32]([C:34]1[CH:35]=[CH:36][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:42][CH:43]=1)[CH3:33])=[O:30]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57900983methyl 4-{(1S)-1-[({2,5-dichloro-4-[(3-chlorophenyl)(hydroxy)methyl]-3-thienyl}carbonyl)amino]ethyl}benzoate

Product 1

HCID 57900990methyl 4-[(1S)-1-({[2,5-dichloro-4-(3-chlorobenzoyl)-3-thienyl]carbonyl}amino)ethyl]benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (114 mg, 0.268 mmol) was added to methyl 4-{(1S)-1-[({2,5-dichloro-4-[(3-chlorophenyl)(hydroxy)methyl]-3-thienyl}carbonyl)amino]ethyl}benzoate from Example 9, Step 1 (89.0 mg, 0.178 mmol) in CH2Cl2 (1.5 mL). After 17 h, the suspension was poured in 20 mL of sat. NaHCO3 containing 7 eq of Na2S2O3 and stirred for 10 min., after which clear layers were obtained. The aqueous layer was extracted with CHCl3, and the combined organics were washed with 5% aq. NaHCO3, water and brine, dried (Na2SO4) and concentrated. The crude product was purified by Combi Flash chromatography system (2-8% EtOAc/toluene in 20 min.) to afford the desired product as a white solid.

Workup

  1. customafter which clear layers were obtained
  2. extractionThe aqueous layer was extracted with CHCl3
  3. washthe combined organics were washed with 5% aq. NaHCO3, water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by Combi Flash chromatography system (2-8% EtOAc/toluene in 20 min.)

Sources & evidence

ORD record
ord-955ad2997ef441a88457d1f2877d7232
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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