Triethylamine → HCID 10097552, compound

HRID 1726517Notes

Reaction equation

HRID 1726517 reaction equation
Cl[S:2]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]([OH:17])=O)(=[O:4])=[O:3].C([N:20]([CH2:23][CH3:24])CC)C.[CH2:25]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([NH2:36])[CH2:32][CH2:31]1)=[O:29])[CH3:26]>ClCCl>[CH2:25]([O:27][C:28]([N:30]1[CH2:31][CH2:32][CH:33]([NH:36][S:2]([C:5]2[C:6]3[C:11](=[C:10]([C:15](=[O:17])[NH:20][CH:23]4[CH2:24][CH2:13][CH2:14][CH2:5][CH:6]4[CH3:7])[CH:9]=[CH:8][CH:7]=3)[CH:12]=[CH:13][CH:14]=2)(=[O:3])=[O:4])[CH2:34][CH2:35]1)=[O:29])[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 15887808HCID 15887808, compound

Product 1

HCID 10097552HCID 10097552, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Chlorosulfonyl-naphthalene-1-carboxylic acid 45 (100 mg, 0.37 mmol) was dissolved in dichloromethane (3 mL). Triethylamine (110 mg, 0.15 mL, 1.11 mmol) was added followed by 4-amino-piperidine-1-carboxylic acid ethyl ester (76 mg, 0.44 mmol). The reaction was stirred for 1 hour at room temperature then diluted with dichloromethane (15 mL). The mixture was charged to a separatory funnel and washed with water, brine and dried over Na2SO4. Flash column chromatography (95:5 dichloromethane:methanol) afforded the title compound as a white solid. Wt.: 20 mg (13%)

Workup

  1. additionThe mixture was charged to a separatory funnel
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-84fef7cca8424940b49b8fcb274de4af
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

Loading…