Triethylamine → HCID 57687747, compound

HRID 1880817Notes

Reaction equation

HRID 1880817 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C@H:12]([NH:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:13][OH:14])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:28]([C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1)#[N:29].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C@H:12]([N:15]([S:36]([C:33]1[CH:32]=[CH:31][C:30]([C:28]#[N:29])=[CH:35][CH:34]=1)(=[O:38])=[O:37])[CH2:16][CH:17]([CH3:18])[CH3:19])[CH2:13][OH:14])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 57687748HCID 57687748, compound

Product 1

HCID 57687747HCID 57687747, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-(6-Hydroxy-5-isobutylamino-hexyl)-carbamic acid tert-butyl ester (4) (1.85 g) was dissolved in 50 mL CH2Cl2. Triethylamine (1.05 eq) and 4-cyano benzene sulfonylchloride (1 eq) were added and the mixture was stirred overnight. Saturated NaHCO3 (50 mL) was added, the mixture was well shaken. Organic layer was separated, dried on MgSO4, filtrated and evaporated. The crude compound was purified by column chromatography using EtOAc-heptane (1-3) as the eluent. Fractions containing the product were evaporated yielding (1.06 g, 36%) of a solid.

Workup

  1. stirringthe mixture was well shaken
  2. customOrganic layer was separated
  3. customdried on MgSO4
  4. filtrationfiltrated
  5. customevaporated
  6. customThe crude compound was purified by column chromatography
  7. additionFractions containing the product
  8. customwere evaporated

Sources & evidence

ORD record
ord-cfed406870aa4d9ea3762938a64db134
Source dataset
uspto-grants-2012_11
Patent number
US08318779B2

Reaction notes

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