Hydrochloric Acid → HCID 58709717, compound

HRID 1170416Notes

Reaction equation

HRID 1170416 reaction equation
[NH4+].C(OC(=O)[NH:8][C@@:9]([CH3:32])([CH2:26][O:27][P:28]([OH:31])([OH:30])=[O:29])[CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]2[O:19][C:18]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[N:17][C:16]=2[CH:25]=1)(C)(C)C.Cl>C(OCC)C>[NH2:8][C@:9]([CH3:32])([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]2[O:19][C:18]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[N:17][C:16]=2[CH:25]=1)[CH2:26][O:27][P:28](=[O:29])([OH:31])[OH:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86607765HCID 86607765, compound

Product 1

HCID 58709717HCID 58709717, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of [(R)-1-Methyl-3-(2-pentyl-benzoxazol-5-yl)-1-phosphonooxymethyl-propyl]-carbamic acid tert-butyl ester ammonium salt (18 mg, 0.0369 mmol) in diethyl ether (2 ml) was treated with 2M HCl in diethyl ether and stirred for 2 hours at RT. The reaction was quenched by the addition of a solution of 28% aqueous ammonium hydroxide (2 ml), methanol (2 ml) and DCM (1 ml). After evaporation of the solvents in vacuum the residue was purified using preparative reversed phase chromatography (X-Terra, C-18, eluent: gradient of 10 mM NH4HCO3 in water/acetonitrile. The title compound was obtained as an amorphous solid. MS(MH−) 269.3.

Workup

  1. customThe reaction was quenched by the addition of a solution of 28% aqueous ammonium hydroxide (2 ml), methanol (2 ml) and DCM (1 ml)
  2. customAfter evaporation of the solvents in vacuum the residue
  3. customwas purified

Sources & evidence

ORD record
ord-a2718e0f8f954a5cad66abee60b35134
Source dataset
uspto-grants-2010_11
Patent number
US07825260B2

Reaction notes

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