Triethylamine → HCID 59840877, compound

HRID 1875715Notes

Reaction equation

HRID 1875715 reaction equation
[CH2:1]([O:8][NH:9][CH2:10][C@@H:11]([C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH2:20][CH2:19]1)=[O:17])[CH2:12][CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:39](OC=O)(=[O:41])C>C1COCC1>[CH2:1]([O:8][N:9]([CH2:10][C@@H:11]([C:16]([N:18]1[CH2:19][CH2:20][N:21]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH2:22][CH2:23]1)=[O:17])[CH2:12][CH:13]([CH3:15])[CH3:14])[CH:39]=[O:41])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75269Acetic-formic anhydrideHCID 16737732HCID 16737732, compound

Product 1

HCID 59840877HCID 59840877, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S)—N-(benzyloxy)-2-{[4-(4-methoxyphenyl)piperazin-1-yl]carbonyl}-4-methylpentan-1-amine (122 mg; 0.29 mmol; 1.0 eq.) and triethylamine (123 μL; 0.86 mmol; 3.0 eq.) in THF (2 mL) was added formic acetic anhydride (63 mg, 0.72 mmol, 2.5 eq., prepared as described in Krimen et al., in Organic Syntheses Coll. Vol 6, p 8. The solution was stirred for 4.5 h at room temperature. The solvents were evaporated and the residue purified by column chromatography (Silicagel, 1/1 EtOAc/c-Hex) to give the title product as a colorless oil (105 mg, 81%). HPLC, Rt: 3.17 min (purity: 100%). M+ (LC-MS (ESI)): 454.4.

Workup

  1. customprepared
  2. customThe solvents were evaporated
  3. customthe residue purified by column chromatography (Silicagel, 1/1 EtOAc/c-Hex)

Sources & evidence

ORD record
ord-c4e068aba4fb49e6be68c5cb77349288
Source dataset
uspto-grants-2012_11
Patent number
US08309579B2

Reaction notes

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