Hydrochloric Acid → HCID 44156360, compound

HRID 2092717Notes

Reaction equation

HRID 2092717 reaction equation
O[C@@H:2]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@@H:3]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)[CH2:4][NH:5][CH3:6].Cl.C(N(S(F)(F)[F:30])CC)C.O>C(Cl)Cl>[F:30][C@H:2]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@@H:3]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)[CH2:4][NH:5][CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 20631903HCID 20631903, compound

Product 1

HCID 44156360HCID 44156360, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of the (2S,3R)-3-hydroxy-N-methyl-2-(naphthalen-2-yl)-3-phenylpropan-1-amine.HCl (48.6 mg, 0.167 mmol) in 2 mL of DCM was added neat diethylaminosulfur trifluoride (0.073 mL, 0.67 mmol). The reaction mixture was stirred for 1 h at room temperature. Water (10 mL) was added very cautiously (exothermic reaction), and the aqueous reaction mixture was filtered through 0.45μ Teflon filters. The pure product was isolated by reverse phase HPLC (Vydac 2.2×25 cm, C-8, elution with a gradient of 10% B-100% B in 90 min, B=80% aq. CH3CN with 0.1% TFA, A=H2O with 0.1% TFA); FR=8 mL/min; λmax=254 nm; RT=48.5 min). Evaporation of the solvent from product containing HPLC fractions furnished the product as a gummy residue that turned into a white solid after conversion to a hydrochloride salt and drying under high vacuum. Yield 8.9 mg, 18.2%. MCJ001-F-55: 1H NMR (CD3OD) δ 7.87-7.72 (m, 4H), 7.67 (s, 1H), 7.52-7.43 (m, 3H), 7.32-7.13 (m, 4H), 5.81 (dd, J=46.5, 8.5 Hz, 1H), 3.91-3.65 (m, 4H), 2.72 (s, 3H); MS (ESI): m/z 294.12 (M+1)+; [α]D20 c 0.03, 9:1 EtOH:H2O). MCJ001-C1-SS: 1H NMR (CD3OD) δ 7.85-7.69 (m, 4H), 7.66 (s, 1H), 7.49-7.41 (m, 3H), 7.33-7.04 (m, 4H), 5.38 (d, J=9.4 Hz, 1H), 4.07-3.-3.07 (m, 4H), 2.69 (s, 3H); MS: m/z 310.30 (M+1)+; [α]20D c,+9.5 (c 0.335, 9:1 EtOH:H2O)

Workup

  1. custom(exothermic reaction)
  2. filtrationthe aqueous reaction mixture was filtered through 0.45μ Teflon filters
  3. customThe pure product was isolated by reverse phase HPLC (
  4. washVydac 2.2×25 cm, C-8, elution with a gradient of 10% B-100% B in 90 min
  5. customEvaporation of the solvent from product
  6. additioncontaining HPLC fractions
  7. customfurnished the product as a gummy residue that
  8. customdrying under high vacuum

Sources & evidence

ORD record
ord-79e2e4c864f24f098ad383357d4c1626
Source dataset
uspto-grants-2013_05
Patent number
US08440724B2

Reaction notes

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