Di-tert-butyl dicarbonate → HCID 86626940, compound

HRID 1695317Notes

Reaction equation

HRID 1695317 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([O:14][CH2:15][CH2:16][NH:17][CH2:18][CH2:19][O:20][C:21]2[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[C:24]([C:30]([O:32][CH3:33])=[O:31])=[CH:23][C:22]=2[O:34][CH3:35])=[C:7]([O:36][CH3:37])[CH:6]=1)=[O:4].C([O-])(O)=O.[Na+].[O:43](C(OC(C)(C)C)=O)[C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=O>C1COCC1>[C:47]([O:46][C:44]([N:17]([CH2:18][CH2:19][O:20][C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[C:24]([C:30]([O:32][CH3:33])=[O:31])=[CH:23][C:22]=1[O:34][CH3:35])[CH2:16][CH2:15][O:14][C:8]1[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][C:7]=1[O:36][CH3:37])=[O:43])([CH3:50])([CH3:49])[CH3:48]

Participants

5

Reactant 3

HCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 86626941HCID 86626941, compound

Product 1

HCID 86626940HCID 86626940, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N-di[2-(4-methoxycarbonyl-2-methoxy-5-nitrophenyl-oxy)ethyl]amine, compound 9, (crude, 4.16 mmol) and NaHCO3 (210 mg, 2.50 mmol) was suspended in THF, and treated with (BOC)2O (999 mg, 4.58 mmol) at 0° C. and stirring was continued at rt for 3 h. After removal of THF, the residue was partitioned between H2O and EtOAc (100/100 mL). Aqueous layer was further extracted with EtOAc (2×50 mL). The combined EtOAc layers were washed with brine (80 mL), dried (MgSO4), and concentrated. Purification of the residue by flash chromatography (silica gel, 6:4 hexanes/EtOAc) yielded N-tert-butoxycarbonyl-N,N-d i[2-(4-methoxycarbonyl-2-methoxy-5-nitro-phenyloxy)ethyl]amine, compound 10, as light yellow solid: 1HNMR (300 MHz, CDCl3) δ 1.44 (s, 9H), 3.77 (m, 4H), 3.83, 3.86 and 3.87 (3×s, 12H), 4.20 and 4.26 (2×t, J=3.9 Hz, 4H), 6.97 and 6.99 (2×s, 2H), 7.36 and 7.40 (2×s, 2H); EIMS m/z 646 ([M]++Na).

Workup

  1. customAfter removal of THF
  2. customthe residue was partitioned between H2O and EtOAc (100/100 mL)
  3. extractionAqueous layer was further extracted with EtOAc (2×50 mL)
  4. washThe combined EtOAc layers were washed with brine (80 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification of the residue by flash chromatography (silica gel, 6:4 hexanes/EtOAc)

Sources & evidence

ORD record
ord-3866f45b57b546958a083d13125f6d5f
Source dataset
uspto-grants-2012_04
Patent number
US08163736B2

Reaction notes

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