Sodium Acetate → HCID 68627573, compound

HRID 656806Notes

Reaction equation

HRID 656806 reaction equation
[CH:1]1([C:4]2[C:5]([N:31]([S:40]([CH3:43])(=[O:42])=[O:41])[CH2:32][CH:33]([OH:39])[CH2:34][NH:35][C:36](=[O:38])[OH:37])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([O:18][C:19]5[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=5)=[CH:14][CH:13]=4)=[C:9]([C:26](=[O:29])[NH:27][CH3:28])[C:8]=3[CH:30]=2)[CH2:3][CH2:2]1.[CH:44]1[CH:45]=[CH:46][NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[CH3:55]C([O-])=O.[Na+]>C(Cl)Cl>[C:45]([O:38][C:36](=[O:37])[NH:35][CH2:34][C:33](=[O:39])[CH2:32][N:31]([C:5]1[C:4]([CH:1]2[CH2:2][CH2:3]2)=[CH:30][C:8]2[C:9]([C:26](=[O:29])[NH:27][CH3:28])=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]4[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=4)=[CH:14][CH:13]=3)[O:11][C:7]=2[CH:6]=1)[S:40]([CH3:43])(=[O:41])=[O:42])([CH3:44])([CH3:46])[CH3:55]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 68640999HCID 68640999, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 68627573HCID 68627573, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

step 2—A solution of 36 (0.178 g, 0.267 mmol), PCC (0.114 g, 0.680 mmol), NaOAc (214 mg) and DCM (8 mL) was added stirred overnight. The solvent was evaporated and the crude product purified on a SiO2 column eluting with an EtOAc/hexane gradient (0 to 50% EtOAc) to afford 0.081 g of [3-({5-cyclopropyl-2-[4-(4-fluoro-phenoxy)-phenyl]-3-methylcarbamoyl-benzofuran-6-yl}-methanesulfonyl-amino)-2-oxo-propyl]-carbamic acid tert-butyl ester (38).

Workup

  1. customThe solvent was evaporated
  2. customthe crude product purified on a SiO2 column
  3. washeluting with an EtOAc/hexane gradient (0 to 50% EtOAc)

Sources & evidence

ORD record
ord-a87acaea116c49c399dfc1c23979b33b
Source dataset
uspto-grants-2011_12
Patent number
US08071797B2

Reaction notes

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