Trifluoroacetic acid → HCID 15942507, compound

HRID 2360645Notes

Reaction equation

HRID 2360645 reaction equation
[CH:1]1([O:6][C:7](=[O:43])[C@H:8]([CH:37]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]2)[NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:36])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](=[O:35])[NH:26][O:27]C(OCC(C)C)C)=[CH:13][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl.CO>[CH:1]1([O:6][C:7](=[O:43])[C@H:8]([CH:37]2[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]2)[NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:36])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](=[O:35])[NH:26][OH:27])=[CH:13][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86636514HCID 86636514, compound

Product 1

HCID 15942507HCID 15942507, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Material from step 6b (50 mg, 0.083 mmol, 1 eq) was dissolved in DCM/methanol (2 mL:2 mL) and stirred with TFA (1.0 mL) for 2 h. The resulting salt was concentrated, dissolved in methanol and purified by preparative HPLC to yield compound (86). LCMS purity 100%, m/z 502 [M++H]+, 1H NMR (300 MHz, MeOD), δ: 1.28-1.98 (26H, m, 13×CH2), 2.10-2.15 (2H, m, CH2), 2.40 (2H, t, J=7.8 Hz, CH2), 3.81 (1H, d, J=3.9 Hz, CH), 4.21 (2H, m, CH2), 5.01 (1H, s, CH), 5.23-5.25 (1H, m, CH), 7.43 (2H, d, J=8.4 Hz, Ar—H), 7.68 (2H, d, J=8.7 Hz, Ar—H)

Workup

  1. concentrationThe resulting salt was concentrated
  2. dissolutiondissolved in methanol
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-b1ab4128d55340aaa25cd9ed582b5178
Source dataset
uspto-grants-2014_04
Patent number
US08686032B2

Reaction notes

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