Triethylamine → HCID 18661252, compound

HRID 2255222Notes

Reaction equation

HRID 2255222 reaction equation
[C@@H:1]12[C:10](=[O:11])[O:9][C:7](=[O:8])[C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.[NH2:12][C@H:13]([C:24]([NH:26][CH3:27])=[O:25])[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1.C(N(CC)CC)C.S(=O)(=O)(O)[O-].[K+]>CN(C)C=O.O.C(OCC)(=O)C>[CH3:27][NH:26][C:24](=[O:25])[C@H:13]([CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)[NH:12][C:7]([C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C@@H:1]1[C:10]([OH:9])=[O:11])=[O:8]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 516920Potassium bisulfateHCID 641660Hexahydrophthalic anhydride, cis-HCID 1450557553708-63-7

Product 1

HCID 18661252HCID 18661252, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 0.281 g (1.82 mmol) of cis-1,2-cyclohexanedicarboxylic anhydride and 0.47 g of the hydrochloride salt of L-Trp-NHMe in 0.5 mL of dimethylformamide 0.51 mL of triethylamine was added at room temperature. After 2 hr of stirring the resulting mixture was diluted to 10 mL with water and 25 mL of ethyl acetate was added. The resulting mixture was acidified to pH =2 with lo% potassium bisulfate and the organic phase was washed with water (2×15 ml), saturated sodium chloride and dried over anhydrous magnesium sulfate and evaporated to dryness. The title compound 35 was purified by crystallization from an ethyl acetate-hexane mixture. Yield 48%; mp=105°-112° C.; Rf (G)=0.65, 0.61.

Workup

  1. additionwas added at room temperature
  2. additionwas added
  3. washthe organic phase was washed with water (2×15 ml), saturated sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated to dryness
  6. customThe title compound 35 was purified by crystallization from an ethyl acetate-hexane mixture

Sources & evidence

ORD record
ord-9fbe37df9b444fe294c26ff7dc744053
Source dataset
uspto-grants-1993_08
Patent number
US05239078

Reaction notes

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