Sodium Bicarbonate → HCID 58052426, compound

HRID 2190207Notes

Reaction equation

HRID 2190207 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]3[C:45]([C:46](=[O:49])[NH:47][CH3:48])=[C:44]([C:50]4[CH:55]=[CH:54][C:53]([CH3:56])=[CH:52][CH:51]=4)[O:43][C:7]3=[N:8][C:9]=2[N:10]([CH2:15][CH2:16][CH2:17][C@H:18]([CH3:42])[C:19]([O:21][CH2:22][O:23][P:24]([O:34]CC2C=CC=CC=2)([O:26]CC2C=CC=CC=2)=[O:25])=[O:20])[S:11]([CH3:14])(=[O:13])=[O:12])[CH2:3][CH2:2]1.C([O-])(O)=O.[Na+]>CCOC(C)=O.[Pd]>[CH:1]1([C:4]2[CH:5]=[C:6]3[C:45]([C:46](=[O:49])[NH:47][CH3:48])=[C:44]([C:50]4[CH:55]=[CH:54][C:53]([CH3:56])=[CH:52][CH:51]=4)[O:43][C:7]3=[N:8][C:9]=2[N:10]([CH2:15][CH2:16][CH2:17][C@H:18]([CH3:42])[C:19]([O:21][CH2:22][O:23][P:24]([OH:26])([OH:34])=[O:25])=[O:20])[S:11]([CH3:14])(=[O:12])=[O:13])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 58052352HCID 58052352, compound

Product 1

HCID 58052426HCID 58052426, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(S)-((bis(benzyloxy)phosphoryl)oxy)methyl 5-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(p-tolyl)furo[2,3-b]pyridin-6-yl)methylsulfonamido)-2-methylpentanoate (10 mg, 0.012 mmol) and Pd—C (10% wt) (1.3 mg) in EtOAc (250 μL) with NaHCO3 (1.045 mg, 0.012 mmol) was placed under N2 and then evacuated and backfilled with H2 and kept under an H2 balloon at RT for 2 hrs (trace COOH side prod.) Filtered through 0.45μ PTFE filter to give (S)-(phosphonooxy)methyl 5-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-(p-tolyl)furo[2,3-b]pyridin-6-yl)methylsulfonamido)-2-methylpentanoate.

Workup

  1. customevacuated
  2. customat RT
  3. customfor 2 hrs
  4. filtrationFiltered through 0.45μ PTFE
  5. filtrationfilter

Sources & evidence

ORD record
ord-e5429f365ac741fc8ab3668a37b67ef6
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

Loading…