Triethylamine → HCID 11628462, compound

HRID 558024Notes

Reaction equation

HRID 558024 reaction equation
[C:1]([O:4][C@H:5]1[C@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@@H:12]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[O:11][C@H:7](SCC)[C@H:6]1[N:27]=[N+:28]=[N-:29])(=[O:3])[CH3:2].C1C(=O)N(I)C(=[O:33])C1.CC[N:40]([CH2:43][CH3:44])CC.[C:45]1(C)C=[CH:49][CH:48]=[CH:47][CH:46]=1.[CH3:52][CH2:53][O:54][C:55](C)=[O:56]>C(Cl)Cl.C(S([O-])(=O)=O)(F)(F)F.[Ag+]>[C:1]([O:4][C@H:5]1[C@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@@H:12]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:24])[CH3:25])([CH3:22])[CH3:21])[O:11][C@H:7]([O:33][CH2:44][CH2:43][NH:40][C:55]([O:54][CH2:53][C:52]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:56])[C@H:6]1[N:27]=[N+:28]=[N-:29])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 120273N-IodosuccinimideHCID 11503270HCID 11503270, compoundHCID 21584019Toluene ethylacetate

Product 1

HCID 11628462HCID 11628462, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Compound 23 (527 g, 1.18 mmol) was dissolved in CH2Cl2 (10 mL) containing MS (4 Å). Benzyl N-(2-hydroxyethyl) carbamate (300 mg, 1.54 mmol) was added and the mixture was stirred under argon at −20° C. for 30 min before NIS (345 mg, 1.53 mmol) and AgOTf (cat) was added. After 30 min the reaction mixture was neutralized with Et3N, diluted with CH2Cl2, washed with Na2S2O3 (10%), filtered (silica) and concentrated. Chromatography (1:0→1:1 toluene-EtOAc) gave 24 (595 mg, 1.02 mmol, 86%); [α]D+46° (c 1.0, CHCl3); 13C NMR δ −5.38, −5.34 (CH3Si), 18.4 ((CH3)3CSi), 20.6, 20.8 (CH3CO), 25.9 ((CH3)3CSi), 40.7 (HOCH2CH2NH), 61.6, 62.6, 66.6, 66.9, 67.6, 71.3, 71.8 (C-2-6, PhCH2O, OCH2CH2N), 98.0 (C-1), 128.2, 128.3, 128.6, 136.5 (aromatic C), 156.4 (NHCOOCH2), 169.6, 170.1 (CH3CO); 1H NMR δ 0.03 (s, 3H), 0.04 (s, 3H), 0.89 (s, 9H), 2.03 (s, 3H), 2.09 (s, 3H), 2.35 (s, 1H) 3.32-3.40 (m, 1H), 3.44-3.52 (m, 1H), 3.58-3.66 (m, 3H), 3.72-3.80 (m, 2H), 3.98-4.00 (m, 1H), 5.11 (s, 2H), 5.18-5.23 (m, 1H), 5.32-5.36 (m, 1H), 7.16-7.36 (m, 5H).

Workup

  1. additioncontaining MS (4 Å)
  2. additionwas added
  3. washwashed with Na2S2O3 (10%)
  4. filtrationfiltered (silica)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4532697655c1433a8ab95187fe8d63a8
Source dataset
uspto-grants-2011_11
Patent number
US08062641B2

Reaction notes

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