Diisopropylethylamine → HCID 67541222, compound

HRID 1400220Notes

Reaction equation

HRID 1400220 reaction equation
O.O[N:3]1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[S:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[C:22]1[C:30]1C=[CH:37][CH:36]=[CH:35][C:31]=1[C:32]([OH:34])=O.[NH2:39][CH:40]([CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[CH:41]([OH:45])[C:42]([NH2:44])=[O:43]>CN(C=O)C.O.C(Cl)CCl>[NH2:44][C:42](=[O:43])[CH:41]([OH:45])[CH:40]([NH:39][C:32]([C:31]1[C:30]([C:22]2[S:21][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[N:23]=2)=[N:3][CH:37]=[CH:36][CH:35]=1)=[O:34])[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2426202-(1,3-benzothiazol-2-yl)benzoic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 138823553-Amino-2-hydroxy-4-phenylbutanamide

Product 1

HCID 67541222HCID 67541222, compoundYield 81.2%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

0.58 g 1-Hydroxybenzotriazole hydrate, 0.75 ml diisopropylethylamin (DIPEA) and 0.82 g EDC successively were added to a solution of 2-(1,3-benzothiazol-2-yl)benzoic acid (1.0 g, 3.90 mmol) in a mixture of 1.5 ml DMF und 20 ml THF at 5° C., and stirred at 5° C. for 1 hour. 3-Amino-2-hydroxy-4-phenylbutanamide (0.8 g, 3.9 mmol) was added, and the reaction mixture stirred for 1 hour at 5° C. and then over night at room temperature. For work up water was added under cooling, the precipitate formed filtered off with suction and dried to give 1.33 g of the title compound.

Workup

  1. stirringthe reaction mixture stirred for 1 hour at 5° C.
  2. waitover night at room temperature
  3. temperatureunder cooling
  4. customthe precipitate formed
  5. filtrationfiltered off with suction
  6. customdried

Sources & evidence

ORD record
ord-48f4e840a9f5451f8dd49618ca255c21
Source dataset
uspto-grants-2014_12
Patent number
US08906941B2

Reaction notes

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