Trifluoroacetic acid → HCID 67033017, compound

HRID 2167915Notes

Reaction equation

HRID 2167915 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[O:21][CH2:20][CH2:19][N:18]([CH2:22][CH2:23][O:24][P:25](=[O:28])([OH:27])[OH:26])[CH2:17]2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(OC1C=CC(C2OCCN(CCOP(=O)(OC(C)(C)C)OC(C)(C)C)C2)=CC=1)CCCCCCC.[C:65]([OH:71])([C:67]([F:70])([F:69])[F:68])=[O:66]>C(Cl)Cl>[F:68][C:67]([F:70])([F:69])[C:65]([OH:71])=[O:66].[CH2:1]([O:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]2[O:21][CH2:20][CH2:19][N:18]([CH2:22][CH2:23][O:24][P:25](=[O:26])([OH:28])[OH:27])[CH2:17]2)=[CH:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 67031802HCID 67031802, compoundHCID 67032644HCID 67032644, compound

Product 1

HCID 67033017HCID 67033017, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phosphoric acid mono-{2-[2-(4-octyloxy-phenyl)-morpholin-4-yl]-ethyl}ester: A solution of phosphoric acid di-tert-butyl ester 2-[2-(4-octyloxy-phenyl)-morpholin-4-yl]-ethyl ester (0.69 g; 1.31 mmol) in TFA (3 mL) and CH2Cl2 (3 mL) was stirred at RT for 1 hour. Subsequently, the reaction mixture was concentrated in vacuo and the residue treated with iPr2O. The precipitate was collected by filtration and dried in vacuo overnight to afford phosphoric acid mono-{2-[2-(4-octyloxy-phenyl)-morpholin-4-yl]-ethyl}ester trifluoroacetic acid salt (0.42 g) 1H NMR (400 MHz, DMSO-d6) δ ppm 0.63-0.79 (m, 3H) 0.98-1.32 (m, 9H) 1.45-1.58 (m, 2H) 2.86-3.07 (m, 2H) 3.13-3.28 (m, 2H) 3.29-3.47 (m, 2H) 3.68-3.83 (m, 3H) 3.89-4.06 (m, 3H) 4.57 (d, J=10.53 Hz, 1H) 6.77 (d, J=8.43 Hz, 2H) 7.10 (d, J=8.43 Hz, 2H).

Workup

  1. concentrationSubsequently, the reaction mixture was concentrated in vacuo
  2. additionthe residue treated with iPr2O
  3. filtrationThe precipitate was collected by filtration
  4. customdried in vacuo overnight

Sources & evidence

ORD record
ord-61bcaba0d2b0490b88e5b4d0c36ca4d7
Source dataset
uspto-grants-2015_06
Patent number
US09045441B2

Reaction notes

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