Triethylamine → HCID 54128708, compound

HRID 965470Notes

Reaction equation

HRID 965470 reaction equation
C(O)(=O)C.C(O)(=O)C.[C:9]([C:11]1[CH:12]=[C:13]([C:17]([NH:19][CH2:20][C:21]2[CH:22]=[C:23]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:24]=[CH:25][CH:26]=2)=[O:18])[CH:14]=[CH:15][CH:16]=1)#[N:10].Cl.[NH2:35][OH:36].C(N(CC)CC)C.CCOC(C)=O.CCCCCC>CCO.CC(O)=O>[NH2:10][C:9](=[N:35][OH:36])[C:11]1[CH:12]=[C:13]([C:17]([NH:19][CH2:20][C:21]2[CH:22]=[C:23]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:24]=[CH:25][CH:26]=2)=[O:18])[CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 443297Hydroxyamine hydrochloride2×HCID 21226206Ethyl acetate hexaneHCID 131720748HCID 131720748, compound

Product 1

HCID 54128708HCID 54128708, compoundYield 110.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

A solution of the compound of Example 19 (0.491 g, 1.3 mmol), hydroxylamine hydrochloride (0.092 g, 1.3 mmol), and triethylamine (0.18 mL, 1.3 mmol) in absolute EtOH (10 mL) was heated to reflux (86°-90° C.). After 5 hours, TLC [1:1 EtOAc/hexane (10 mL) and 5 drops of AcOH] showed that starting material was still present. Additional hydroxylamine hydrochloride (0.038 g, 0.5 eq) and triethylamine (0.09 mL) was added. After 40 minutes, the TLC showed no difference. The reaction was concentrated in vacuo to give a pale yellow oil (0.53 g). The oil was purified by column chromatography [50 g silica gel, 3% MeOH/CH2 Cl2 (500 mL) followed by 10% MeOH/CH2Cl2 (150 mL)] and the desired product was collected in 85% yield (0.42 g). NMR was consistent with proposed structure.

Workup

  1. temperatureto reflux (86°-90° C.)
  2. waitAfter 40 minutes
  3. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-a47be46d7891470980338ee6f67361fb
Source dataset
uspto-grants-1998_06
Patent number
US05773646

Reaction notes

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