Triethylamine → HCID 69697466, compound

HRID 1814380Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:39])[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:25])(=[O:24])[NH:11][C@H:12]([C:21](=O)[NH2:22])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:6]([O:26][CH2:27][CH2:28][C:29]2[CH:38]=[CH:37][CH:36]=[C:35]3[C:30]=2[CH:31]=[CH:32][CH:33]=[N:34]3)[CH:5]=1.CCN(CC)CC.O(C(C(F)(F)F)=O)C(C(F)(F)F)=O>C1COCC1>[CH3:1][O:2][C:3](=[O:39])[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:24])(=[O:25])[NH:11][C@H:12]([C:21]#[N:22])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:6]([O:26][CH2:27][CH2:28][C:29]2[CH:38]=[CH:37][CH:36]=[C:35]3[C:30]=2[CH:31]=[CH:32][CH:33]=[N:34]3)[CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-((S)-2-tert-butoxycarbonyl-1-carbamoyl-ethylsulfamoyl)-3-(2-quinolin-5-yl-ethoxy)-benzoic acid methyl ester (1.20 g, 2.20 mmol) in dry THF (10 mL) at 0° C. was added Et3N (0.80 mL, 5.50 mmol). A solution of (CF3CO)2O in THF (0.5 M, 0.37 mL, 2.60 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 (50 mL). Drying and removal of solvents under vacuum gave 0.90 g (76%) of 4-((S)-2-tert-butoxycarbonyl-1-cyano-ethylsulfamoyl)-3-(2-quinolin-5-yl-ethoxy)-benzoic acid methyl ester as a tan solid. MS m/z 540.3 (M+1).

Workup

customthe ice bath was removed
temperatureto warm up to room temperature over 4 h
additionThe reaction mixture was worked up by addition of EtOAc (100 mL)
washby washing the organic phase with saturated NaHCO3 (50 mL)
customDrying
customremoval of solvents under vacuum

Sources & evidence

ORD record: ord-f4732a2832dc47fbbd90e7aade70b23e
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875765B2

Reaction notes

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