Triethylamine → HCID 10857986, compound

HRID 1007050Notes

Reaction equation

HRID 1007050 reaction equation
[CH:1]([C:3]1[NH:4][CH:5]=[C:6]2[O:11][CH2:10][CH2:9][O:8][C:7]=12)=[O:2].[O:12](C(OC(C)(C)C)=O)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=O.C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[C:13]([N:4]1[CH:5]=[C:6]2[O:11][CH2:10][CH2:9][O:8][C:7]2=[C:3]1[CH:1]=[O:2])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 11073620HCID 11073620, compound

Product 1

HCID 10857986HCID 10857986, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of aldehyde 19 (0.8 g, 5.2 mmol) in dichloromethane was added (BOC)2O (1.1 g, 5.2 mmol), triethylamine (1.1 g, 10.4 mmol), and 4-dimethylaminopyridine (DMAP) (61 mg, 0.5 mmol). The reaction mixture was stirred for 3 h and concentrated under reduced pressure. The residue was purified by chromatography on silica gel using hexane/ethyl acetate (3:1) as eluent to yield a colorless crystalline product (1.2 g, 90%): mp 94-95° C.; 1H NMR (300 MHz, CDCl3) δ10.24 (s, 1H), 6.88 (s, 1H), 4.38 (m, 2H), 4.22 (m, 2H), 1.60 (s, 9H); 13C NMR (75 MHz, CDCl3) δ180.9, 148.8, 143.2, 134.2, 116.6, 107.9, 85.1, 66.1, 64.9, 27.9; FT-IR (CDCl3) 2930, 2859, 1653, 1544, 1460, 1380, 1322 cm−1; Anal. Calcd for C12H15NO5: C, 56.91; H 5.97; N, 5.53. Found: C, 56.90; H, 5.80; N, 5.73.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-46c3e925e00548cfbba3aeeb393211ec
Source dataset
uspto-grants-2004_09
Patent number
US06791738B2

Reaction notes

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