Triethylamine → HCID 57989013, compound

HRID 1689501Notes

Reaction equation

HRID 1689501 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:19][C@H:20]([OH:32])[C:21]1[C:29]2[S:28][C:27](=[O:30])[NH:26][C:25]=2[C:24]([OH:31])=[CH:23][CH:22]=1)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].FC(F)(F)C(O)=O.[F:40][C:41]([F:56])([F:55])[C:42]([N:44]1[CH2:49][C:48]2([CH2:54][CH2:53][NH:52][CH2:51][CH2:50]2)[O:47][CH2:46][CH2:45]1)=[O:43].C(N(CC)CC)C>CC#N>[OH:32][C@H:20]([C:21]1[C:29]2[S:28][C:27](=[O:30])[NH:26][C:25]=2[C:24]([OH:31])=[CH:23][CH:22]=1)[CH2:19][N:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:52]1[CH2:53][CH2:54][C:48]2([O:47][CH2:46][CH2:45][N:44]([C:42](=[O:43])[C:41]([F:40])([F:55])[F:56])[CH2:49]2)[CH2:50][CH2:51]1)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 57989278HCID 57989278, compoundHCID 866367502,2,2-Trifluoro-1-(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone trifluoroacetate

Product 1

HCID 57989013HCID 57989013, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of (R)-tert-butyl 9-bromononyl(2-hydroxy-2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl)carbamate (example 183-222, step b) (1.68 g) in MeCN (8 mL) was added dropwise to a solution of 2,2,2-trifluoro-1-(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone trifluoroacetate (example 12, step d) (1.18 g) and triethylamine (0.81 mL) in MeCN (8 mL). The resulting mixture was stirred at 80° C. for 18 h. The reaction was allowed to cool to RT and the solvent was removed in vacuo. The brown residue was taken up in DCM and the organic layer was washed with water (×2) and brine, dried over sodium sulphate, filtered and evaporated in vacuo. The brown foam was purified by silica gel chromatography eluting with 0-10% MeOH/DCM to give the subtitled compound as a white solid. Yield 500 mg.

Workup

  1. temperatureto cool to RT
  2. customthe solvent was removed in vacuo
  3. washthe organic layer was washed with water (×2) and brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe brown foam was purified by silica gel chromatography
  8. washeluting with 0-10% MeOH/DCM

Sources & evidence

ORD record
ord-c25cc064f57744e0afe5f18998e6ab09
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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