1,4-Dioxane hydrochloride → HCID 68719269, compound

HRID 2246700Notes

Reaction equation

HRID 2246700 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([O:11][P:12]([CH2:21][C@H:22]([OH:32])[CH2:23][NH:24]C(OC(C)(C)C)=O)([CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:13])[O:3]1.[ClH:33].O1CCOCC1>O1CCOCC1>[ClH:33].[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([O:11][P:12]([CH2:21][C@H:22]([OH:32])[CH2:23][NH2:24])([CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:13])[O:3]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 68720237HCID 68720237, compound

Product 1

HCID 68719269HCID 68719269, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ((R)-3-tert-butoxycarbonylamino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid 3-oxo-1,3-dihydro-isobenzofuran-1-yl ester (140 mg, 0.3 mmol) in 2 mL dioxane was added a 4N HCl/dioxane solution (5.0 mL, 20 mmol). After 2 h the reaction mixture was concentrated in vacuo and the resulting residue taken up in ethyl acetate and was concentrated in vacuo to yield ((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid 3-oxo-1,3-dihydro-isobenzofuran-1-yl ester hydrochloride (120 mg, 0.3 mmol). 1H NMR (CD3OD, 300 MHz): δ 7.92 (m, 1H), 7.73 (m, 2H), 7.15 (m, 1H), 4.40 (m, 1H), 3.4-3.22 (m, 1H), 3.20-3.04 (m, 1H), 2.01-1.8 (m, 6H), 1.75-1.60 (m, 4H), 1.50-1.0 (m, 7H). 31P NMR (CD3OD, 300 MHz): δ 61.4, 60.6. LC/MS m/z: [M+H]+=368

Workup

  1. concentrationAfter 2 h the reaction mixture was concentrated in vacuo
  2. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-ba9b33fac9b84dffbb23c614053bc14c
Source dataset
uspto-grants-2010_03
Patent number
US07687540B2

Reaction notes

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