Trifluoroacetic acid methylene chloride → HCID 59364374, compound

HRID 426073Notes

Reaction equation

HRID 426073 reaction equation
[CH3:1][O:2][C:3]([NH:5][CH2:6][CH2:7][O:8][C@@H:9]([C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[CH:40]=1)[CH2:10][CH2:11][N:12]([CH2:36][CH2:37][CH3:38])[C:13](=[O:35])[NH:14][C@@H:15]([CH2:28][C@H:29]1[CH2:34][CH2:33][CH2:32][O:31][CH2:30]1)[CH2:16][N:17](C)[C:18](=O)OCC[Si](C)(C)C)=[O:4].C(O)(C(F)(F)F)=O.C(Cl)Cl>>[Cl:45][C:41]1[CH:40]=[C:39]([C@H:9]([O:8][CH2:7][CH2:6][NH:5][C:3](=[O:4])[O:2][CH3:1])[CH2:10][CH2:11][N:12]([CH2:36][CH2:37][CH3:38])[C:13](=[O:35])[NH:14][C@@H:15]([CH2:28][C@H:29]2[CH2:34][CH2:33][CH2:32][O:31][CH2:30]2)[CH2:16][NH:17][CH3:18])[CH:44]=[CH:43][CH:42]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 66704627HCID 66704627, compound

Product 1

HCID 59364374HCID 59364374, compoundYield 105.6%

Procedure

2-(trimethylsilyl)ethyl (S)-2-(3-((R)-3-(2-(methoxycarbonylamino)ethoxy)-3-(3-chlorophenyl)propyl)-3-propylureido)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl(methyl)carbamate (31 mg) was treated with (V/V) 20% TFA/CH2Cl2 (2 mL) for 1 hr. The excess reagent was evaporated and the crude material was purified via preparative HPLC to afford the desired product (25.7 mg). LC-MS (3 min) tR=1.36 m/z=527. 1H NMR (CD3OD) d 7.25-7.35 (m, 4H), 4.30 (t, 1H), 4.10 (m, 1H), 3.89 (dd, 1H), 3.83 (m, 1H), 3.63 (s, 3H), 3.36-3.42 (m, 4H), 3.27 (m, 3H), 3.05-3.17 (m, 3H), 2.97 (t, 1H), 2.71 (s, 3H), 1.82-1.92 (m, 3H), 0.91 (t, 3H).

Workup

  1. customThe excess reagent was evaporated
  2. customthe crude material was purified via preparative HPLC

Sources & evidence

ORD record
ord-d4a0f3ce065e4823b0f056ac10ffd55b
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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