Triethylamine → HCID 178454050, compound

HRID 2225220Notes

Reaction equation

[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7].C(N(CC)CC)C.ClC(OCC(C)C)=O.[NH2:33][C@@H:34]1[CH2:39][CH2:38][C@H:37]([NH:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:36][CH2:35]1>C1COCC1.C(Cl)Cl>[F:16][C:2]([F:1])([F:17])[C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[C:6]([NH:8][CH2:9][C:10]([NH:33][C@@H:34]1[CH2:39][CH2:38][C@H:37]([NH:40][C:41](=[O:47])[O:42][C:43]([CH3:45])([CH3:44])[CH3:46])[CH2:36][CH2:35]1)=[O:12])=[O:7]

Participants

Conditions

Temperature: 0 °C

Procedure

2-(3-(trifluoromethyl)-benzamido)acetic acid (277 mg, 1.12 mmol, 1.2 eq) and triethylamine (0.15 mL, 1.12 mmol, 1.2 eq) were dissolved in THF (15 mL) at room temperature under nitrogen. Cooled to 0° C. Added isobutyl chloroformate (0.16 μL, 1.12 mmol, 1.2 eq) dropwise. Stirred for 10 mintues followed by the dropwise addition of tert-butyl cis-4-amino-cyclo-hexylcarbamate (200 mg, 0.93 mmol, 1 eq) in THF ((5 mL). Warmed to room temperature. Worked up after 3 hours by adding methylene chloride (25 mL) and rinsing 3 times with saturated sodium bicarbonate (25 mL). The organic layer was dried (sodium sulfate) and stripped to give an oil. Purified over silica gel in 1:1 hexanes/ethyl acetate to give tert-butyl cis-4-(2-(3-(trifluoromethyl)-benzamido)acetamido)cyclohexylcarbamate (350 mg) as an oil. MS found: (M+Na)+=466.20.

Workup

temperatureWarmed to room temperature
washrinsing 3 times with saturated sodium bicarbonate (25 mL)
dry with materialThe organic layer was dried (sodium sulfate)
customto give an oil
customPurified over silica gel in 1:1 hexanes/ethyl acetate

Sources & evidence

ORD record: ord-2327d45c74dd49b0b7808d4d77b40594
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378409B2

Reaction notes

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