Trifluoroacetic acid → HCID 9908836, compound

HRID 1393629Notes

Reaction equation

HRID 1393629 reaction equation
C([O:5][C:6](=[O:33])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C@H:12]([NH:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[C:13](=[O:21])[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:26]([O:25][C:23]([NH:22][C@H:12]([C:13](=[O:21])[NH:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([OH:33])=[O:5])=[O:24])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 9890197HCID 9890197, compound

Product 1

HCID 9908836HCID 9908836, compoundYield 120.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ester 51 (76 mg, 0.167 mmol) in CH2Cl2 (5 mL) was added TFA (0.5 mL) and the reaction solution stirred for 5 h. The solution was concentrated under reduced pressure to give crude 52 as a white solid (80 mg) which was used in the next step without purification. TLC Rf 0.32 (5% MeOH/CH2Cl2); 1H-NMR (400 MHz, DMSO-d6) δ 11.93 (br s, 1H), 9.99 (s, 1H), 7.58 (d, 2H), 7.55 (d, 1H), 7.35 (m, 4H), 7.29 (t, 2H), 7.03 (t, 1H), 5.02 (m, 2H), 4.11 (br dd, 1H), 2.17 (t, 2H), 1.59 (m, 2H), 1.48 (m, 2H), 1.22 (m, 4H).

Workup

  1. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-24a2b11116bb4277baff9fa84c907c1c
Source dataset
uspto-grants-2008_03
Patent number
US07345174B2

Reaction notes

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