HCID 72247373, compound → HCID 74948506, compound

HRID 2191005Notes

Reaction equation

HRID 2191005 reaction equation
[CH2:1]([O:3][P:4]([CH:9]=[CH:10][CH:11]1[CH:18]2[CH:14]([O:15]C(C)(C)[O:17]2)[CH:13]([N:21]2[C:25]3[N:26]=[CH:27][N:28]=[C:29]([NH:30][C:31](=[O:38])[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:24]=3[N:23]=[N:22]2)[O:12]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]>C(O)(C(F)(F)F)=O.O>[CH2:6]([O:5][P:4]([CH:9]=[CH:10][CH:11]1[CH:18]([OH:17])[CH:14]([OH:15])[CH:13]([N:21]2[C:25]3[N:26]=[CH:27][N:28]=[C:29]([NH:30][C:31](=[O:38])[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:24]=3[N:23]=[N:22]2)[O:12]1)(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

4

Reactant 1

HCID 72247373HCID 72247373, compound

Product 1

HCID 74948506HCID 74948506, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 6.4 (170 mg, 0.31 mmol) was dissolved in 90% TFA in H2O (10 mL). The mixture was stirred for 30 min and concentrated down under reduced pressure. The residue was subjected to a silica gel column chromatography eluting with 10% MeOH in CH2Cl2 to yield compound 6.5 (110 mg, 70% yield). 1HNMR (300 MHz, CD3OD) δ 1.24-1.28 (m, 6H), 3.96-4.06 (m, 4H), 4.63 (t, 1H, J=5.1), 4.73 (s, 1H), 4.97 (t, 1H, J=4.2), 5.92-6.04 (m, 1H), 6.5 (d, 1H, J=3.9), 6.81-6.96 (m, 1H), 7.55-8.12 (m, 5H), 8.77 (s, 1H). LRMS (ESI) MH+ C21H25N6O7P requires 505.2. Found 504.9.

Workup

  1. concentrationconcentrated down under reduced pressure
  2. washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-6b7aa8b53afd46d09fad62765257a6af
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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