Diisopropylethylamine → Tert-butyl trans-{4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl)cyclohexyl}acetate

HRID 1035699Notes

Reaction equation

HRID 1035699 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:24]([C:31]1[S:35][C:34]([NH2:36])=[N:33][N:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[CH2:24]([C:31]1[S:35][C:34]([NH:36][C:19]([C:18]2[CH:17]=[CH:16][C:15]([CH:12]3[CH2:13][CH2:14][CH:9]([CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:10][CH2:11]3)=[CH:23][CH:22]=2)=[O:21])=[N:33][N:32]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 7548235-Benzyl-1,3,4-thiadiazol-2-amineHCID 666854144-(4-Tert-butoxycarbonylmethylcyclohexyl)benzoic acid

Product 1

HCID 66739902Tert-butyl trans-{4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl)cyclohexyl}acetateYield 34%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.45 g of 4-(4-tert-butoxycarbonylmethylcyclohexyl)benzoic acid (1.41 mmol, 1 eq.) is placed in a mixture of 5 mL of dimethylformamide at room temperature. 0.539 g of 5-benzyl-1,3,4-thiadiazol-2-amine (2.82 mmol, 2 eq.), 0.791 g of bromotris-pyrrolidinophosphonium hexafluorophosphonate (1.70 mmol, 1.2 eq.) and 0.49 mL of diisopropylethylamine (2.83 mmol, 2 eq.) are successively added. The reaction mixture is stirred for 16 hours at room temperature, diluted in ethyl acetate and washed three times with water. The organic phase is concentrated. The residue is taken up and washed with ethanol, filtered and dried. 0.236 g of tert-butyl {4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl]cyclohexyl}acetate is obtained.

Workup

  1. washwashed three times with water
  2. concentrationThe organic phase is concentrated
  3. washwashed with ethanol
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-9f102501a5854ad1bfc91bf51fb59a82
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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