Hydrochloric Acid → HCID 44155980, compound

HRID 1891033Notes

Reaction equation

HRID 1891033 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.S(Cl)([Cl:26])=O.CCO>ClCCl.O>[Cl:26][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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 24386Thionyl ChlorideHCID 20631902HCID 20631902, compound

Product 1

HCID 44155980HCID 44155980, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (2R,3S)-3-hydroxy-N-methyl-2-(naphthalen-2-yl)-3-phenylpropan-1-amine.HCl (70 mg, 0.24 mmol) and 1 mL of thionyl chloride in 3 mL of dry dichloromethane (DCM) was stirred at room temperature for 30 minutes under nitrogen. The mass spectrum (MS) of the crude indicated clean and complete conversion. The volatiles were evaporated at reduced pressure. The product MCJ001-C1-RR was washed with dry diethyl ether, and dried under high vacuum. A white solid was obtained (74 mg, 90%) which was judged pure by 1H NMR and MS. 1H NMR (CD3OD) δ 7.84-7.71 (m, 4H), 7.65 (s, 1H), 7.49-7.41 (m, 3H), 7.32-7.10 (m, 4H), 5.37 (d, J=9.4 Hz, 1H), 3.86-3.70 (m, 4H), 2.70 (s, 3H); MS (ESI): m/z 310.30 (M+1)+; [α]D20 −11.0 (c 0.2, 9:1 EtOH:H2O).

Workup

  1. customThe volatiles were evaporated at reduced pressure
  2. washThe product MCJ001-C1-RR was washed with dry diethyl ether
  3. customdried under high vacuum
  4. customA white solid was obtained (74 mg, 90%) which

Sources & evidence

ORD record
ord-3c254179dd974daf953e7167418740dd
Source dataset
uspto-grants-2013_08
Patent number
US08507500B2

Reaction notes

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