Water → DCCI HOBt

HRID 1352186Notes

Reaction equation

HRID 1352186 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[N:9]([OH:10])[N:8]=[N:7][C:5]=2[CH:6]=1.O.[CH2:12]1[CH2:17][CH2:16][CH:15]([N:18]=[C:19]=[N:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH2:14][CH2:13]1>C(Cl)Cl>[CH2:24]1[CH2:23][CH2:22][CH:21]([N:20]=[C:19]=[N:18][CH:15]2[CH2:16][CH2:17][CH2:12][CH2:13][CH2:14]2)[CH2:26][CH2:25]1.[CH:1]1[CH:2]=[CH:3][C:4]2[N:9]([OH:10])[N:8]=[N:7][C:5]=2[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 757711-Hydroxybenzotriazole

Product 1

HCID 21712060DCCI HOBt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Boc protected amino acid (14.2 mmole) in DCM (35 ml) is cooled to 0° C. HOBt.H2O (12.9 mmole, 1.75 g) and DCC (15.5 mmole, 3.2g) are added to a reaction mixture and vigorously stirred for 1 h. Deprotected peptide (after removal of the Boc group) dissolved in DCM (20 ml) and TEA (18.1 mmole) is introduced and the mixture is stirred for an additional 30 min. at 0° C. The cooling bath is removed and the reaction is left overnight at room temperature.

Workup

  1. customDeprotected peptide (after removal of the Boc group)
  2. dissolutiondissolved in DCM (20 ml)
  3. stirringthe mixture is stirred for an additional 30 min. at 0° C
  4. customThe cooling bath is removed
  5. waitthe reaction is left overnight at room temperature

Sources & evidence

ORD record
ord-62fc25ca46ac418ab376e91f110b5a29
Source dataset
uspto-grants-2007_05
Patent number
US07220725B2

Reaction notes

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