Bromotrimethylsilane → HCID 178447111, compound

HRID 1364013Notes

Reaction equation

HRID 1364013 reaction equation
Br[Si](C)(C)C.[C:6]([NH:9][C@@H:10]1[C@@H:15]([NH:16][C:17]([NH:26]C(OC(C)(C)C)=O)=[N:18]C(OC(C)(C)C)=O)[CH2:14][C:13]([P:34]([O:39]CC)(=[O:38])[O:35]CC)=[CH:12][C@H:11]1[O:42][CH:43]([CH2:46][CH3:47])[CH2:44][CH3:45])(=[O:8])[CH3:7]>C(Cl)(Cl)Cl>[C:6]([NH:9][C@@H:10]1[C@@H:15]([NH:16][C:17]([NH2:26])=[NH:18])[CH2:14][C:13]([P:34]([O-:39])(=[O:35])[O-:38])=[CH:12][C@H:11]1[O:42][CH:43]([CH2:44][CH3:45])[CH2:46][CH3:47])(=[O:8])[CH3:7].[NH4+:9].[NH4+:9]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 178476969HCID 178476969, compound

Product 1

HCID 178447111HCID 178447111, compoundYield 217.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Bromotrimethylsilane (5 mL, 38 mmol) was added to a cold (0° C.) solution of 12b (287 mg, 0.46 mmol) in CHCl3 (20 mL). The mixture was stirred for 24 h at room temperature, and then concentrated under reduced pressure. The residue was taken up in water (15 mL), stirred for 2 h at room temperature, and subjected to lyophilization. The residue was purified on a C18 column (0.1 M aqueous NH4HCO3 solution) to afford ammonium phosphonate 13b (132 mg, 72% yield). White solid, mp 220-223° C.; [α]D20=−55.3 (c=1.5, H2O); IR (neat) 3512, 2901, 1716, 1101 cm−1; 1H NMR (600 MHz, D2O) δ 6.12 (1 H, d, JP-2=19.0 Hz), 4.12 (1 H, d, J=6.9 Hz), 3.80 (1 H, dd, J=10.0, 5.0 Hz), 3.71-3.62 (1 H, m), 3.41 (1 H, br s), 2.62-2.59 (1 H, m), 2.28-2.23 (1 H, m), 1.91 (3 H, s), 1.46-1.44 (3H, m), 1.34-1.28 (1 H, m), 0.77 (3 H, t, J=7.3 Hz), 0.72 (3 H, t, J=7.3 Hz); 13C NMR (150 MHz, D2O) δ 174.5, 156.6, 134.3 (C-1, d, JP-1=168 Hz), 132.7, 84.2, 76.3, 55.2, 51.0, 30.8, 25.5, 25.2, 21.8, 8.6, 8.2; 31P NMR (162 MHz, D2O) δ10.92; HRMS calcd for C14H26N4O5P [M+H−2 NH4]+: 361.1652, found: 361.1637. Anal. Calcd for C14H33N6O5P.(2H2O): C, 38.88; H, 8.62; N, 19.43. Found: C, 38.74; H, 8.71; N, 19.39.

Workup

  1. concentrationconcentrated under reduced pressure
  2. stirringstirred for 2 h at room temperature
  3. customThe residue was purified on a C18 column (0.1 M aqueous NH4HCO3 solution)

Sources & evidence

ORD record
ord-6400fba7ab154b2ca937989841dda7b7
Source dataset
uspto-grants-2011_02
Patent number
US07888337B2

Reaction notes

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