Triethylamine → HCID 68838555, compound

HRID 660684Notes

Reaction equation

HRID 660684 reaction equation
OC(C(F)(F)F)=O.[NH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[S:21](=[O:23])(=[O:22])[N:20]([CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:19](=[O:30])[CH2:18]2)=[C:13]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:12]=1.C(N(CC)CC)C.[CH:46]1([N:52]=[C:53]=[O:54])[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1>O1CCOCC1>[CH2:32]([O:31][C:13]1[CH:12]=[C:11]([CH2:10][CH2:9][NH:8][C:53]([NH:52][CH:46]2[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]2)=[O:54])[CH:16]=[CH:15][C:14]=1[N:17]1[CH2:18][C:19](=[O:30])[N:20]([CH2:24][CH2:25][Si:26]([CH3:27])([CH3:28])[CH3:29])[S:21]1(=[O:23])=[O:22])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18502Cyclohexyl isocyanateHCID 866325725-[4-(2-Aminoethyl)-2-benzyloxyphenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one TFA Salt

Product 1

HCID 68838555HCID 68838555, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

To 5-[4-(2-aminoethyl)-2-benzyloxyphenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (0.25 g, 0.434 mmol) (Example 67, step A) in 5 mL dioxane is added triethylamine (0.12 mL, 0.87 mmol), followed by cyclohexyl isocyanate (0.11 mL, 0.87 mmol) and the mixture heated to 85° C. for 1 h. The reaction mixture is concentrated and then partitioned between EtOAc and 1N HCl. The combined organic layers are washed with saturated sodium bicarbonate and brine, dried, and evaporated to afford a crude orange oil which is purified by flash chromatography to afford the title compound as a foam.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. custompartitioned between EtOAc and 1N HCl
  3. washThe combined organic layers are washed with saturated sodium bicarbonate and brine
  4. customdried
  5. customevaporated
  6. customto afford a crude orange oil which
  7. customis purified by flash chromatography

Sources & evidence

ORD record
ord-1467649d87b140ae9daed622cbb2a088
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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