Triethylamine → HCID 20774775, compound

HRID 398287Notes

Reaction equation

HRID 398287 reaction equation
[NH2:1][C@@H:2]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)[CH2:3][OH:4].C(N(CC)CC)C.[Cl:25][C:26]1[S:30][C:29]([S:31](Cl)(=[O:33])=[O:32])=[CH:28][CH:27]=1>C(Cl)Cl>[C:14]([O:13][C:11]([N:8]1[CH2:7][CH2:6][CH:5]([CH:2]([NH:1][S:31]([C:29]2[S:30][C:26]([Cl:25])=[CH:27][CH:28]=2)(=[O:33])=[O:32])[CH2:3][OH:4])[CH2:10][CH2:9]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27339255-Chlorothiophene-2-sulfonyl chlorideHCID 66929718HCID 66929718, compound

Product 1

HCID 20774775HCID 20774775, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of tert-butyl 4-[(1S)-1-amino-2-hydroxyethyl]-1-piperidinecarboxylate (0.107 g, 0.44 mmol), triethylamine (0.046 g, 0.46 mmol) and methylene chloride (5 mL) cooled to 0° C., was added 5-chlorothiophene-2-sulfonyl chloride (0.095 g, 0.44 mmol) as a solution dissolved in 2 mL methylene chloride, dropwise by pipet. After 15 min, the ice bath was removed and the reaction allowed to attain 25° C. and stir overnight. The reaction was quenched by pouring it into saturated sodium bicarbonate solution (25 mL) and additional methylene chloride (15 mL). The organic phase was separated and washed sequentially with 1N HCl solution, H2O, brine and dried over MgSO4. The organic phase was filtered and evaporated to produce a crude oil that was flash chromatographed using ethyl acetate-hexane, 1—1 as eluent. This produced the title compound as a solid (0.109 g, 58%). MS (+APCI) 442.18 ([M+NH4]+); 386.08; 357.01; 325.07; 307.01; 285.06. Anal. Calc'd for C16H25ClN2O5S2: C, 45.22; H, 5.93; N, 6.59; Found: C, 45.31; H, 5.87; N, 6.4

Workup

  1. customthe ice bath was removed
  2. customto attain 25° C.
  3. customThe reaction was quenched
  4. additionby pouring it into saturated sodium bicarbonate solution (25 mL) and additional methylene chloride (15 mL)
  5. customThe organic phase was separated
  6. washwashed sequentially with 1N HCl solution, H2O, brine
  7. dry with materialdried over MgSO4
  8. filtrationThe organic phase was filtered
  9. customevaporated
  10. customto produce a crude oil that
  11. customchromatographed

Sources & evidence

ORD record
ord-d2f8b7231e174e4292bcfbddf57303c3
Source dataset
uspto-grants-2003_08
Patent number
US06610734B2

Reaction notes

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