HCID 86636752, compound → HCID 49855236, compound

HRID 471085Notes

Reaction equation

HRID 471085 reaction equation
[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[F:31][C:32]1[CH:54]=[CH:53][C:52]([CH2:55][N:56]2[CH2:76][CH2:75][C:59]3([O:64][CH2:63][CH2:62][N:61]([C:65]([C:67]4[N:68]=[C:69]([CH:72]([CH3:74])[CH3:73])[S:70][CH:71]=4)=[O:66])[CH2:60]3)[CH2:58][CH2:57]2)=[CH:51][C:33]=1[CH2:34][CH2:35][NH:36][CH2:37][C@@H:38]([C:40]1[C:48]2[S:47][C:46](=[O:49])[NH:45][C:44]=2[C:43]([OH:50])=[CH:42][CH:41]=1)[OH:39]>C(=O)(O)[O-].[Na+]>[F:31][C:32]1[CH:54]=[CH:53][C:52]([CH2:55][N:56]2[CH2:57][CH2:58][C:59]3([O:64][CH2:63][CH2:62][N:61]([C:65]([C:67]4[N:68]=[C:69]([CH:72]([CH3:74])[CH3:73])[S:70][CH:71]=4)=[O:66])[CH2:60]3)[CH2:75][CH2:76]2)=[CH:51][C:33]=1[CH2:34][CH2:35][NH:36][CH2:37][C@@H:38]([C:40]1[C:48]2[S:47][C:46](=[O:49])[NH:45][C:44]=2[C:43]([OH:50])=[CH:42][CH:41]=1)[OH:39]

Participants

3

Reactant 1

HCID 86636752HCID 86636752, compound

Product 1

HCID 49855236HCID 49855236, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

(R)-7-(2-(2-fluoro-5-((4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethylamino)-1-hydroxyethyl)-4-hydroxybenzo[d]thiazol-2(3H)-one di(1S)-(+)-10-camphorsulfonic acid salt (Example 47B) (4.1 g) was partioned between freshly distilled 2-methyl-THF (100 mL) and saturated sodium bicarbonate solution (100 mL). The layers were separated and the organic layer washed with saturated sodium bicarbonate solution (100 mL), brine (100 mL), dried over sodium sulphate, filtered and evaporated in vacuo. The resulting glassy solid was triturated thrice with ether to give the subtitle compound as a white solid. Yield 2.6 g.

Workup

  1. customThe layers were separated
  2. washthe organic layer washed with saturated sodium bicarbonate solution (100 mL), brine (100 mL)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe resulting glassy solid was triturated thrice with ether

Sources & evidence

ORD record
ord-a5b9864c3d3344519be96647b07ea83a
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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