HCID 86636752, compound → HCID 49855236, compound

HRID 1689316Notes

Reaction equation

HRID 1689316 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-cf651b3a51ce4cff8441787497f0f924
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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