Triethylamine → HCID 24994045, compound

HRID 1673242Notes

Reaction equation

HRID 1673242 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[N:12]=[CH:11][O:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:13]1[N:18]=[C:17]2[O:19][C:20]([CH3:25])([CH3:24])[CH2:21][CH:22]([NH2:23])[C:16]2=[CH:15][C:14]=1[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1.[F:33][C:34]([F:41])([F:40])[CH:35]([OH:39])[C:36](O)=[O:37].CCN(CC)CC.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl.CC(O)C.CCO>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[N:12]=[CH:11][O:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:13]1[N:18]=[C:17]2[O:19][C:20]([CH3:24])([CH3:25])[CH2:21][CH:22]([NH:23][C:36](=[O:37])[CH:35]([OH:39])[C:34]([F:41])([F:40])[F:33])[C:16]2=[CH:15][C:14]=1[C:26]1[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 2448963,3,3-Trifluoro-2-hydroxypropanoic acidHCID 2724699PyBOPHCID 67019988HCID 67019988, compound

Product 1

HCID 24994045HCID 24994045, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Step B (107 mg, 0.23 mmol), 3,3,3-trifluoro-2-hydroxypropionic acid (39 mg, 0.27 mmol), and NEt3 (63 μL, 0.45 mmol) in 10 mL of CH2Cl2 was added PyBOP (140 mg, 0.27 mmol). After stirring at rt for 16 h, the mixture was concentrated. Chromatography on a Biotage 25+M cartridge using 1:1 v/v EtOAc/hexanes as the eluant afforded two enantiomeric mixtures, which were subsequently resolved (the one having higher Rf value on TLC was resolved by AD using 13% EtOH/hex, and the other by AD using 20% IPA/hept) to afford the title compounds.

Workup

  1. concentrationthe mixture was concentrated
  2. customafforded two enantiomeric mixtures, which

Sources & evidence

ORD record
ord-e166cc9e22ca49b4bb77af0cd578e688
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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