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

HRID 2289210Notes

Reaction equation

HRID 2289210 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) δ 9.62 (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-42edbe3d05e64866b23413ff56930a50
Source dataset
uspto-grants-2000_07
Patent number
US06090947

Reaction notes

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