Triethylamine → HCID 86740965, compound

HRID 365042Notes

Reaction equation

HRID 365042 reaction equation
[CH2:1]([C:11]1[CH:21]=[CH:20][C:14]([C:15]([N:17]([OH:19])C)=[O:16])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].ON1C2C=CC=C[C:26]=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.O(N)C.C(N(CC)CC)C>C(Cl)Cl>[CH:1](/[C:11]1[CH:21]=[CH:20][C:14]([C:15]([NH:17][O:19][CH3:26])=[O:16])=[CH:13][CH:12]=1)=[CH:2]/[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 521874O-Methylhydroxylamine hydrochlorideHCID 136728004-Decyl-N-hydroxy-N-methylbenzamide

Product 1

HCID 86740965HCID 86740965, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the benzoic acid prepared in Example 1 Part C (2.0 g, 7.68 mM) in dry CH2Cl2 (20 ml) was added 1-hydroxybenzotriazole (1.25 g, 9.22 mM, 1.2 eq.) and N,N'-dicyclohexylcarbodiimide (1.90 g, 9.22 mM, 1.2 eq.) and the mixture stirred for 1 hour at room temperature. Methoxylamine hydrochloride (1.28 g, 15.36 mM. 2 eq.) and triethylamine (2.14 ml, 15.36 mM, 2 eq.) were added, the mixture stirred for 3 hours at room temperature, then filtered, evaporated, taken up in ethyl acetate and filtered again. The organic phase was washed successively with 5% KHSO4, saturated NaHCO3 and brine, then dried over anhydrous Na2SO4 and evaporated to an oil. The crude oil was flash chromatographed on LPS-1 silica gel eluting with (7:3) hexane-ethyl acetate. Product containing fractions were evaporated to give 2.023 g (91%) of the desired title product, 1.664 g of cis isomer, 359 mg of trans isomer as a low melting white solid with consistent NMR (CDCl3, 60 MHz) spectral data. TLC (1:1) EtOAc-Hex, Rf =0.39 UV and PMA.

Workup

  1. stirringthe mixture stirred for 3 hours at room temperature
  2. filtrationfiltered
  3. customevaporated
  4. filtrationfiltered again
  5. washThe organic phase was washed successively with 5% KHSO4, saturated NaHCO3 and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated to an oil
  8. customchromatographed on LPS-1 silica gel eluting with (7:3) hexane-ethyl acetate
  9. additionProduct containing fractions
  10. customwere evaporated

Sources & evidence

ORD record
ord-a2c5f68cf3f04bbca62fca4ed29a32ce
Source dataset
uspto-grants-1986_08
Patent number
US04607053

Reaction notes

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