Triethylamine → HCID 59840877, compound

HRID 1672169Notes

Reaction equation

HRID 1672169 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, p8. 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-181d5aa86614430f92a58e87642716b0
Source dataset
uspto-grants-2011_08
Patent number
US07998964B2

Reaction notes

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