Dicyclohexylcarbodiimide → 4-Tert-butoxycarbonylamino-1-methyl-1h-pyrrole-2-carboxylic acid benzotriazol-1yl ester

HRID 1265486Notes

Reaction equation

HRID 1265486 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1N=[C:11]([C:15]([OH:17])=[O:16])[N:12]([CH3:14])[CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[N:20]1.[CH2:28]1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:28]=[C:11]([C:15]([O:17][N:19]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]=[N:20]2)=[O:16])[N:12]([CH3:14])[CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 27572264-[(tert-Butoxycarbonyl)amino]-1-methyl-1H-imidazole-2-carboxylic acid

Product 1

HCID 27559874-Tert-butoxycarbonylamino-1-methyl-1h-pyrrole-2-carboxylic acid benzotriazol-1yl esterYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The Boc-imidazole-acid 12 (2 g, 8.3 mmol) was in dissolved in 10 ml of DMF and 1-hydroxybenzotriazole was added (1.2 g, 9 mmol) followed by DCC (2.4 g, 9 mmol). After 6 hours the precipitate was removed by filtration and washed with 4 ml of DMF. The DMF solution was added dropwise to 250 ml of well stirred ice water and the resulting precipitate was collected by vacuum filtration. The filter cake was ground and dried in vacuo over P2O5 to give (2.7 g, 89%) of 13 as a pale yellow power contaminated with a small amount of DCU (2.7 g, 89%). 1H NMR (DMSO-d6) δ9.62 (s, 1H), 7.96 (s, 1H), 7.68 (d, 1H), 7.52 (d, 1H). 7.38 (d, 1H), 7.23 (s, 1H), 3.85 (s, 3H), 1.33 (s, 9H).

Workup

  1. customAfter 6 hours the precipitate was removed by filtration
  2. washwashed with 4 ml of DMF
  3. additionThe DMF solution was added dropwise to 250 ml of well stirred ice water
  4. filtrationthe resulting precipitate was collected by vacuum filtration
  5. dry with materialdried in vacuo over P2O5

Sources & evidence

ORD record
ord-26d5754c3cc94f9eadbde0baea55f31f
Source dataset
uspto-grants-2003_04
Patent number
US06545162B1

Reaction notes

Loading…