Hydrochloric Acid → HCID 86616821, compound

HRID 639136Notes

Reaction equation

HRID 639136 reaction equation
CC([N:5]([C@@H:9]1[C@H:13]([OH:14])[CH2:12][N:11]([CH2:15][CH2:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[N:25]=3)[N:20]=[CH:19][CH:18]=2)[CH2:10]1)C(=O)[O-])(C)C.Cl.O1CCOCC1>CO>[NH2:5][C@@H:9]1[CH2:10][N:11]([CH2:15][CH2:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[N:25]=3)[N:20]=[CH:19][CH:18]=2)[CH2:12][C@@H:13]1[OH:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86616822HCID 86616822, compound

Product 1

HCID 86616821HCID 86616821, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,1-dimethylethyl((3S,4R)-4-hydroxy-1-{2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)carbamate (327 mg, 0.843 mmol) in MeOH (4 mL) at 25° C. was added dropwise a 4M HCl in dioxane solution (1.5 mL, 5.9 mmol). After 12 h, the solution was concentrated and the residue neutralized with excess MP carbonate resin in DCM to afford the title compound (242 mg, quant.) as a yellow oil: LCMS (ES) m/e 289 (M+H).

Workup

  1. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-269d7fce474f4a9cb3b9d4b99182a45b
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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