Triethylamine → Methyl 2,2,12,12-tetramethyl-4,9-dioxo-3,10-dioxa-5,8-diazahexadec-15-ene-7-carboxylate

HRID 2066408Notes

Reaction equation

HRID 2066408 reaction equation
Cl.[NH2:2][CH:3]([CH2:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:4]([O:6][CH3:7])=[O:5].CCN(CC)CC.[C:24](Cl)(=[O:34])[O:25][CH2:26][C:27]([CH3:33])([CH3:32])[CH2:28][CH2:29][CH:30]=[CH2:31]>C1COCC1>[CH3:14][C:13]([CH3:16])([O:12][C:10](=[O:11])[NH:9][CH2:8][CH:3]([C:4]([O:6][CH3:7])=[O:5])[NH:2][C:24](=[O:34])[O:25][CH2:26][C:27]([CH3:33])([CH3:32])[CH2:28][CH2:29][CH:30]=[CH2:31])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18388108H-Dap(boc)-ome hclHCID 577758342,2-Dimethylhex-5-enyl carbonochloridate

Product 1

HCID 57775890Methyl 2,2,12,12-tetramethyl-4,9-dioxo-3,10-dioxa-5,8-diazahexadec-15-ene-7-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 381 mg of methyl 2-amino-3-(tert-butoxycarbonylamino)propanoate hydrochloride, and 1 mL of Et3N in 10 mL of anhydrous THF, was added 1.5 mmol of 2,2-dimethylhex-5-enyl carbonochloridate. The resulting mixture was stirred at rt overnight, then concentrated. The residue was subject to column chromatography on silica gel with heptanes/EtOAc (v/v 7/1) as eluent, giving 500 mg colorless oil (90%). 1NMR (400 MHz, CDCl3) d 5.82 (m, 1H), 5.64 (br s, 1H), 5.02 (dd, 1H, J=13.2, 1.8 Hz), 4.95 (d, 1H, J=8.2 Hz), 4.83 (br s, 1H), 4.39 (br d, 1H, J=6.0 Hz), 3.83 (br s, 2H), 3.80 (s, 3H), 2.55 (m, 2H), 2.02 (m, 2H), 1.43 (s, 9H), 1.35 (m, 2H), 0.91 (s, 6H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-8d3d36ee8f8d40668bdb05a3f6cec459
Source dataset
uspto-grants-2012_10
Patent number
US08293705B2

Reaction notes

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