Triethylamine → HCID 69692575, compound

HRID 1814348Notes

Reaction equation

HRID 1814348 reaction equation
[C:1]([O:5][C:6](=[O:39])[CH2:7][C@H:8]([NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[CH:18][C:17]=1[O:26][CH2:27][CH2:28][C:29]1[CH:38]=[CH:37][CH:36]=[C:35]2[C:30]=1[CH:31]=[CH:32][CH:33]=[N:34]2)(=[O:15])=[O:14])[C:9]([NH2:11])=O)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[C:1]([O:5][C:6](=[O:39])[CH2:7][C@H:8]([NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[CH:18][C:17]=1[O:26][CH2:27][CH2:28][C:29]1[CH:38]=[CH:37][CH:36]=[C:35]2[C:30]=1[CH:31]=[CH:32][CH:33]=[N:34]2)(=[O:14])=[O:15])[C:9]#[N:11])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 69691648HCID 69691648, compound

Product 1

HCID 69692575HCID 69692575, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-3-[4-acetylamino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-succinamic acid tert-butyl ester (0.24 g, 0.40 mmol) in dry THF (10 mL) at 0° C. was added Et3N (0.14 mL, 1.0 mmol). A solution of trifluoroacetic anhydride in THF (0.5 M, 0.50 mmol) was added to the solution dropwise. After 30 min of stirring at 0° C., the ice bath was removed. The reaction mixture was allowed to warm up to room temperature over 4 h. The reaction mixture was worked up by addition of EtOAc (100 mL) then followed by washing the organic phase with saturated NaHCO3. Drying and removal of solvents under vacuum gave 0.20 g (92%) of (S)-3-[4-acetylamino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-3-cyano-propionic acid tert-butyl ester as a tan solid. MS (APCI) m/z 539.1 (M+1).

Workup

  1. customthe ice bath was removed
  2. temperatureto warm up to room temperature over 4 h
  3. additionThe reaction mixture was worked up by addition of EtOAc (100 mL)
  4. washby washing the organic phase with saturated NaHCO3
  5. customDrying
  6. customremoval of solvents under vacuum

Sources & evidence

ORD record
ord-4d0000c6d72a4765a2291a83f0f011a8
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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