HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Aniline → ethyl (2S)-2-anilinopropanoate

HRID 530108
Notes
Print preview

Reaction equation

HRID 530108 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.FC(F)(F)S(O[CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])(=O)=O>ClCCl>[C:2]1([NH:1][C@H:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH3:27])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 4251232Ethyl (-)-lactate triflate

Product 1

HCID 21124386ethyl (2S)-2-anilinopropanoateYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
35 °C

Procedure

To a stirred solution of aniline (4.55 mL, 50 mmol) and triethylamine (7 mL, 50 mmol) in anhydrous dichloromethane (120 mL) was added a solution of ethyl 2-{[(trifluoromethyl)sulfonyl]oxy}propanoate (12.5 g, 50 mmol) in dichloromethane (60 mL) at 0° C. (Ice bath) over a period of 30 minutes under nitrogen. The ice bath was then removed and the reaction mixture was stirred at 35° C. for 2 h. The reaction mixture was cooled to rt, washed with water, dried over sodium sulfate, and evaporated to give desired product as oil (8.9 g, 92%) which was used as such for the next step. 1HNMR (300 MHz, CDCl3): δ 1.19-1.67 (m, 6H), 4.17-4.38 (m, 3H), 6.65-6.80 (m, 3H), 7.20-7.35 (m, 2H).

Workup

  1. customThe ice bath was then removed
  2. temperatureThe reaction mixture was cooled to rt
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-bb4eed0f32d84b60b3e2ecdb0dcbb0dc
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09351974B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes