Trifluoroacetic acid → HCID 86294764, compound

HRID 1507759Notes

Reaction equation

HRID 1507759 reaction equation
C(O)(C(F)(F)F)=O.C([O:12][P:13]([O:20][CH2:21][C:22]1[CH:76]=[CH:75][C:25]([C:26]([O:28][C:29]2[C:33]([O:34][C:35](=[O:56])[C:36]3[CH:41]=[CH:40][C:39]([CH2:42][O:43][P:44]([O:51]C(C)(C)C)([O:46]C(C)(C)C)=[O:45])=[CH:38][CH:37]=3)=[C:32]([C:57](=[O:61])[N:58]([CH3:60])[CH3:59])[N:31]([C:62]3[CH:67]=[CH:66][C:65]([O:68][CH3:69])=[CH:64][CH:63]=3)[C:30]=2[C:70](=[O:74])[N:71]([CH3:73])[CH3:72])=[O:27])=[CH:24][CH:23]=1)([O:15]C(C)(C)C)=[O:14])(C)(C)C>C(Cl)Cl>[P:44]([O:43][CH2:42][C:39]1[CH:38]=[CH:37][C:36]([C:35]([O:34][C:33]2[C:29]([O:28][C:26](=[O:27])[C:25]3[CH:24]=[CH:23][C:22]([CH2:21][O:20][P:13]([OH:15])([OH:14])=[O:12])=[CH:76][CH:75]=3)=[C:30]([C:70](=[O:74])[N:71]([CH3:73])[CH3:72])[N:31]([C:62]3[CH:63]=[CH:64][C:65]([O:68][CH3:69])=[CH:66][CH:67]=3)[C:32]=2[C:57](=[O:61])[N:58]([CH3:60])[CH3:59])=[O:56])=[CH:41][CH:40]=1)([OH:51])([OH:46])=[O:45]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117642791HCID 117642791, compound

Product 1

HCID 86294764HCID 86294764, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (16 mL, 208 mmol) was added dropwise to a solution of 2,5-bis(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-3,4-diyl bis(4-(((di-tert-butoxyphosphoryl)oxy)methyl)benzoate) (64) (88 mg, 0.09 mmol) in DCM (64 mL) the mixture was left to stand for 72 h, and then concentrated in vacuo to afford 2,5-bis(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-3,4-diyl bis(4-((phosphonooxy)methyl)benzoate) (UL1-124) as a yellow oil: m/z 776 (M+H)+ (ES+); 774 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 8.00-7.98 (m, 4H), 7.54-7.52 (m, 4H), 7.20-7.18 (m, 2H), 7.00-6.98 (m, 2H), 4.98-4.96 (d, 4H), 3.79 (s, 3H), 2.89 (s, 6H), 2.74 (s, 6H).

Workup

  1. waitwas left
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3761d2a3a33742f48acfdd98c363391a
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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