Triethylamine → N-Butyl-N-(2,2-dimethoxyethyl)-3-(3-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanamide

HRID 1255335Notes

Reaction equation

HRID 1255335 reaction equation
C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.FC(F)(F)C(O)=O.[CH:26]([C:29]1[S:30][CH:31]=[C:32]([C:34]([N:36]2[CH2:41][C:40]3([CH2:46][CH2:45][N:44]([CH2:47][CH2:48][C:49]4[CH:50]=[C:51]([CH:60]=[CH:61][CH:62]=4)[CH2:52][CH2:53][O:54][CH2:55][CH2:56][C:57](O)=[O:58])[CH2:43][CH2:42]3)[O:39][CH2:38][CH2:37]2)=[O:35])[N:33]=1)([CH3:28])[CH3:27].[CH3:63][O:64][CH:65]([O:72][CH3:73])[CH2:66][NH:67][CH2:68][CH2:69][CH2:70][CH3:71].C(N(CC)CC)C>CN(C=O)C>[CH2:68]([N:67]([CH2:66][CH:65]([O:64][CH3:63])[O:72][CH3:73])[C:57](=[O:58])[CH2:56][CH2:55][O:54][CH2:53][CH2:52][C:51]1[CH:60]=[CH:61][CH:62]=[C:49]([CH2:48][CH2:47][N:44]2[CH2:45][CH2:46][C:40]3([O:39][CH2:38][CH2:37][N:36]([C:34]([C:32]4[N:33]=[C:29]([CH:26]([CH3:27])[CH3:28])[S:30][CH:31]=4)=[O:35])[CH2:41]3)[CH2:42][CH2:43]2)[CH:50]=1)[CH2:69][CH2:70][CH3:71]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 21254099N-(2,2-dimethoxyethyl)butan-1-amineHCID 669641573-(3-(2-(4-(2-Isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanoic acid trifluoroacetate salt

Product 1

HCID 58168512N-Butyl-N-(2,2-dimethoxyethyl)-3-(3-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

T3P (15.67 mL of 1.57M solution in THF) was added dropwise over 15 minutes to a stirred solution of 3-(3-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanoic acid trifluoroacetate salt [Example 34a, step c] (14.4 g) and N-(2,2-dimethoxyethyl)butan-1-amine [J. Am. Chem. Soc. 1949, 71(6), 2272] (3.97 g) and triethylamine (21.83 mL) in DMF (180 mL). The mixture was stirred at 20° C. for 3 hours and then partitioned between ethyl acetate and aqueous brine. The organic layer was washed with aqueous brine (×2), dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure to give the subtitled compound. Yield 15.00 g.

Workup

  1. custompartitioned between ethyl acetate and aqueous brine
  2. washThe organic layer was washed with aqueous brine (×2)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-9702e3b6ae7848e3a072e8f580b39b27
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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