Triethylamine → HCID 22956502, compound

HRID 2231084Notes

Reaction equation

HRID 2231084 reaction equation
[C:1](=[O:11])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[NH2:2].C([N:14]([CH2:17][CH3:18])CC)C.[CH3:19][CH2:20][O:21][C:22]([C@H](OS(C(F)(F)F)(=O)=O)C)=[O:23]>CC.ClCCl>[CH2:20]([O:21][C:22](=[O:23])[CH:17]([NH:14][NH:2][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:11])[CH3:18])[CH3:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12136Benzyl carbamateHCID 10999437Ethyl (R)-2-(trifluoromethylsulfonyloxy)propionate

Product 1

HCID 22956502HCID 22956502, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6324EthaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of benzyl carbamate (665 mg, 4 mmol), triethylamine (1.11 mL) in ethane (4 ml) was added dropwise ethyl O-trifluoromethanesulfonyl-D-lactate at 0° C. The solution was stirred at 0° C. for 15 min then at room temperature for 16 hours. The mixture was diluted with dichloromethane (100 mL), washed with water (50 mL×2), 1% HCl (50 mL×2). The organic layer was dried over anhydrous Na2SO4, filtered, and evaporated to dryness in vacuo to give 570 mg (54% yield) of the title compound. 1H-NMR (500 MHz, CDCl3) δ 1.25-1.40 (m, 6H), 3.68-3.78 (m, 1H), 4.12-4.20 (m, 3H), 5.07-5.15 (m, 1H), 6.45-6.57 (m, 1H), 7.30-7.45 (m, 5H). Analytical HPLC: 5.56 min. LC-MS (ES+): m/e=267 (M+H+).

Workup

  1. waitat room temperature for 16 hours
  2. washwashed with water (50 mL×2), 1% HCl (50 mL×2)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-a122ddfa93bb425e9a9b1fd6a718b5ba
Source dataset
uspto-grants-2002_07
Patent number
US06426413B1

Reaction notes

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