Tetrahydrofuran → HCID 69660093, compound

HRID 722720Notes

Reaction equation

HRID 722720 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[NH:10][CH:9]([CH2:11][CH:12]=[CH2:13])[CH2:8][N:7]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:6]1)=[O:4].[C:24]([N:31]([CH2:36][CH:37]=[CH2:38])CC(O)=O)([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].[CH2:39]([O:43]C1C=CC2C(=CC=CC=2)N1C(OCC(C)C)=O)C(C)C.[CH2:61]1COCC1>>[CH3:1][O:2][C:3]([CH:5]1[N:10]([C:39](=[O:43])[CH:36]([NH:31][C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:37][CH:38]=[CH2:61])[CH:9]([CH2:11][CH:12]=[CH2:13])[CH2:8][N:7]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:6]1)=[O:4]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 1006212-Methylpropyl 2-(2-methylpropoxy)-1(2H)-quinolinecarboxylateHCID 10330883HCID 10330883, compoundHCID 69660992HCID 69660992, compound

Product 1

HCID 69660093HCID 69660093, compoundYield 48%

Procedure

A solution containing 5-allyl-piperazine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester, 3, (1.64 g, 5.1 mmol), N-Boc-allylglycine (3.9 g, 18.0 mmol) and 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline (IIDQ) (5.5 g, 18.0 mmol) in THF was stirred at rt for 48 h. The solvent is removed in vacuo and the residue is purified over silica gel (EtOAc/hexane) to afford 1.28 g (48%) of 4. 1H NMR (CDCl3) δ 7.39 (m, 5H), 5.78 (m, 2H), 5.38–5.10 (m, 6H), 5.0–4.1 (series of m, 5H), 3.73 (br s, 3H), 2.66–2.20 (series of m, 7H), 1.45 (br s, 9H); MS 516 (M+H)+.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is purified over silica gel (EtOAc/hexane)

Sources & evidence

ORD record
ord-c51c7ade55834b3c9ec0c583f087dfa9
Source dataset
uspto-grants-2006_11
Patent number
US07138395B2

Reaction notes

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