Diisopropylcarbodiimide → 2-Methyl-2-[(4-{2-[(8-methylnonanoyl)amino]ethyl}-1,3-thiazol-2-yl)thio]propionic acid

HRID 914506Notes

Reaction equation

HRID 914506 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:5]=[C:6]([S:9][C:10]([CH3:15])([CH3:14])[C:11]([OH:13])=[O:12])[S:7][CH:8]=1.C1C=C2N=NN(O)C2=CC=1.O.C(N=C=NC(C)C)(C)C.[CH3:36][CH:37]([CH3:47])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44](O)=[O:45]>CN(C)C=O>[CH3:14][C:10]([S:9][C:6]1[S:7][CH:8]=[C:4]([CH2:3][CH2:2][NH:1][C:44](=[O:45])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH:37]([CH3:36])[CH3:47])[N:5]=1)([CH3:15])[C:11]([OH:13])=[O:12]

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 1114708-Methylnonanoic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 674005012-{[4-(2-Aminoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid

Product 1

HCID 673973832-Methyl-2-[(4-{2-[(8-methylnonanoyl)amino]ethyl}-1,3-thiazol-2-yl)thio]propionic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-{[4-(2-aminoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid resin (0.30 g) synthesized in Example 483-3 in dimethylformamide (4.0 mL) were added HOBT monohydrate (0.092 g), diisopropylcarbodiimide (0.10 mL) and 8-methylnonanoic acid (0.10 g), and the mixture was stirred at room temperature overnight. The resin was collected by filtration from the reaction mixture, washed three times each with dimethylformamide, tetrahydrofuran and methanol, and vacuum dried to give 2-methyl-2-[(4-{2-[(8-methylnonanoyl)amino]ethyl}-1,3-thiazol-2-yl)thio]propionic acid resin.

Workup

  1. filtrationThe resin was collected by filtration from the reaction mixture
  2. washwashed three times each with dimethylformamide, tetrahydrofuran and methanol, and vacuum
  3. customdried

Sources & evidence

ORD record
ord-13c0139c62d64730a805a3c661d2d840
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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