Triethylamine → HCID 59717996, compound

HRID 1726514Notes

Reaction equation

HRID 1726514 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:16])(=[O:4])=[O:3].C(N(CC)CC)C.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH:35]([NH2:38])[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>ClCCl>[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH:35]([NH:38][S:2]([C:5]2[C:6]3[C:11](=[C:10]([C:15]([OH:17])=[O:16])[CH:9]=[CH:8][CH:7]=3)[CH:12]=[CH:13][CH:14]=2)(=[O:4])=[O:3])[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 15887808HCID 15887808, compound

Product 1

HCID 59717996HCID 59717996, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Chlorosulfonyl-naphthalene-1-carboxylic acid 45 (2.00 g, 7.39 mmol) was dissolved in dichloromethane (30 mL). Triethylamine (2.24 g, 3.1 mL, 22.2 imnol) was added followed by 4-amino-piperidine-1-carboxylic acid tert-butyl ester (1,63 g, 8.13 mmol). The reaction was stirred overnight at room temperature. The reaction was diluted with dichloromethane (50 mL) and charged to a separatory funnel. The organic layer was washed twice with water and brine and dried over MgSO4. Filtration and concentration in vacuo afforded 46 (3.0 g, 93%) as a yellow foam. 1H NMR (300 MHz, d6-DMSO) δ 9.11 (d, 1H), 8.62 (d, 1H), 8.15 (d, 1H), 7.90 (d, 1H), 7.62 (m, 2H), 3.91 (d, 1H), 3.62 (m, 2H), 3.15 (m, 1H), 2.67 (m, 2H), 1.89 (m, 2H), 1.52 (m, 2H), 1.40 (s, 9H); LC/MS m/z 435 (M+H)+.

Workup

  1. additioncharged to a separatory funnel
  2. washThe organic layer was washed twice with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-d8ff386d38fb42b195961867a3b14955
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

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