1,2-Dichloroethane → HCID 57803411, compound

HRID 2103386Notes

Reaction equation

HRID 2103386 reaction equation
[CH2:1]([O:8][C@H:9]1[CH2:13][NH:12][C@H:11]([CH:14]([CH3:16])[CH3:15])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:17][C:18]([F:33])([F:32])[C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[C:22]([NH:24][CH2:25][C:26](O)=[O:27])=[O:23].C(Cl)CCl>ClCCl>[CH2:1]([O:8][C@H:9]1[CH2:13][N:12]([C:26](=[O:27])[CH2:25][NH:24][C:22](=[O:23])[C:21]2[CH:29]=[CH:30][CH:31]=[C:19]([C:18]([F:17])([F:33])[F:32])[CH:20]=2)[C@H:11]([CH:14]([CH3:16])[CH3:15])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 111,2-Dichloroethane2×HCID 2777432((3-(Trifluoromethyl)benzoyl)amino)acetic acid2×HCID 60054959HCID 60054959, compound

Product 1

HCID 57803411HCID 57803411, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S,4R)-4-(Benzyloxy)-2-isopropylpyrrolidine (0.410 g, 1.90 mmol) was dissolved in dichloromethane (30 mL) under nitrogen. (3-Trifluoromethyl-benzoylamino)-acetic acid (0.462 g; 1.90 mmol) was added followed by EDC (0.394 g, 2.06 mmol) and the mixture was stirred at room temperature-overnight. LC/MS revealed the reaction was not yet complete. More (3-Trifluoromethyl-benzoylamino)-acetic acid (0.12 g, 0.48 mmoles) and more EDC (0.30 g, 1.6 mmoles) were added and stirring continued for 3 hours at room temperature, then at reflux for 1.5 hours. The mixture was chromatographed on silica gel eluting with 30% ethyl acetate/hexane to provide 0.66 g (79%) of the coupled product as a colorless oil. LC/MS (M+H)+ m/z=449.2; 1H NMR (CDCl3) δ 8.03 (m, 1H), 7.76 (m, 1H), 7.58 (m, 2H), 7.34 (m, 5H), 4.52 (m, 2H), 4.03-4.34 (m, 4H), 3.65 (m, 1H), 3.48 (m, 1H), 2.54 (m, 1H), 2.12 (m, 1H), 1.92 (m, 1H), 0.92 (d, 3H), 0.77 (d, 3H).

Workup

  1. stirringstirring
  2. temperatureat reflux for 1.5 hours
  3. customThe mixture was chromatographed on silica gel eluting with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-c1496d52b3ba47d0ad3c2fcdae531761
Source dataset
uspto-grants-2009_08
Patent number
US07576089B2

Reaction notes

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