(1S)-(+)-Camphor-10-sulphonic acid → HCID 86636752, compound

HRID 1689314Notes

Reaction equation

HRID 1689314 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[CH2:46][CH2:45][C:29]3([O:34][CH2:33][CH2:32][N:31]([C:35]([C:37]4[N:38]=[C:39]([CH:42]([CH3:44])[CH3:43])[S:40][CH:41]=4)=[O:36])[CH2:30]3)[CH2:28][CH2:27]2)=[CH:21][C:3]=1[CH2:4][CH2:5][NH:6][CH2:7][C@@H:8]([C:10]1[C:18]2[S:17][C:16](=[O:19])[NH:15][C:14]=2[C:13]([OH:20])=[CH:12][CH:11]=1)[OH:9].[C@:47]12([CH2:57][S:58]([OH:61])(=[O:60])=[O:59])[C:54]([CH3:56])([CH3:55])[CH:51]([CH2:52][CH2:53]1)[CH2:50][C:48]2=[O:49]>C(O)(C)C>[C@:47]12([CH2:57][S:58]([OH:61])(=[O:59])=[O:60])[C:54]([CH3:56])([CH3:55])[CH:51]([CH2:52][CH2:53]1)[CH2:50][C:48]2=[O:49].[C@:47]12([CH2:57][S:58]([OH:61])(=[O:59])=[O:60])[C:54]([CH3:56])([CH3:55])[CH:51]([CH2:52][CH2:53]1)[CH2:50][C:48]2=[O:49].[F:1][C:2]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[CH2:27][CH2:28][C:29]3([O:34][CH2:33][CH2:32][N:31]([C:35]([C:37]4[N:38]=[C:39]([CH:42]([CH3:44])[CH3:43])[S:40][CH:41]=4)=[O:36])[CH2:30]3)[CH2:45][CH2:46]2)=[CH:21][C:3]=1[CH2:4][CH2:5][NH:6][CH2:7][C@@H:8]([C:10]1[C:18]2[S:17][C:16](=[O:19])[NH:15][C:14]=2[C:13]([OH:20])=[CH:12][CH:11]=1)[OH:9]

Participants

4

Reactant 2

HCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 49855236HCID 49855236, compound

Product 1

HCID 86636752HCID 86636752, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (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 (4.3 g, 6.42 mmol) (example 47A), (1S)-(+)-10-camphorsulfonic acid (2.98 g, 12.84 mmol) and iso-propanol (300 mL) was heated at 50° C. until a clear solution formed, seeded, allowed to cool to RT and stirred for 4 days. The solid was isolated by filtration, washed with iso-propanol (100 mL), ether (2×200 mL) and sucked dry to give the titled compound as a white crystalline solid. Yield 5.1 g The enantiomeric excess of the title compound is higher than the compound obtained in example 47A. (example 47A=86% ee, title compound >96% ee)

Workup

  1. customformed
  2. temperatureto cool to RT
  3. customThe solid was isolated by filtration
  4. washwashed with iso-propanol (100 mL), ether (2×200 mL)
  5. customsucked dry

Sources & evidence

ORD record
ord-ac61425db4154c74ba3f61856e29791e
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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