Potassium Carbonate → HCID 57988937, compound

HRID 1689502Notes

Reaction equation

HRID 1689502 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-4c0d1628ca86411da6405fcf8a453be3
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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