Potassium Carbonate → HCID 57988937, compound

HRID 471272Notes

Reaction equation

HRID 471272 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C@H:8]([C:44]1[C:52]2[S:51][C:50](=[O:53])[NH:49][C:48]=2[C:47]([OH:54])=[CH:46][CH:45]=1)[CH2:9][N:10]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:43][CH2:42][C:30]2([O:35][CH2:34][CH2:33][N:32](C(=O)C(F)(F)F)[CH2:31]2)[CH2:29][CH2:28]1)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14]>O.CO>[O:35]1[C:30]2([CH2:29][CH2:28][N:27]([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][N:10]([CH2:9][C@H:8]([OH:7])[C:44]3[C:52]4[S:51][C:50](=[O:53])[NH:49][C:48]=4[C:47]([OH:54])=[CH:46][CH:45]=3)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:43][CH2:42]2)[CH2:31][NH:32][CH2:33][CH2:34]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 57989013HCID 57989013, compound

Product 1

HCID 57988937HCID 57988937, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of potassium carbonate (165 mg) in water (24 mL) was added to a solution of (R)-tert-butyl 2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl(9-(4-(2,2,2-trifluoroacetyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)nonyl)carbamate (example 183-222, step c) (495 mg) in MeOH (24 mL). The resulting mixture was stirred at RT for 4 h. Methanol was removed by evaporation under a stream of nitrogen keeping the reaction mixture at 30° C. Water (20 mL) and brine (80 mL) were added and the mixture was extracted with EtOAc (5×60 mL). The combined organic layers were dried over sodium sulphate, filtered and evaporated in vacuo. The brown solid residue was purified by silica gel chromatography eluting with 0-20% (2M NH3 in MeOH)/DCM to give the subtitled compound as a yellow solid. Yield 323 mg.

Workup

  1. customMethanol was removed by evaporation under a stream of nitrogen keeping the reaction mixture at 30° C
  2. additionWater (20 mL) and brine (80 mL) were added
  3. extractionthe mixture was extracted with EtOAc (5×60 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe brown solid residue was purified by silica gel chromatography
  8. washeluting with 0-20% (2M NH3 in MeOH)/DCM

Sources & evidence

ORD record
ord-b66d31aed0b3485ea0999fe45bb71a61
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

Loading…