Hydrochloric Acid → HCID 59118229, compound

HRID 432093Notes

Reaction equation

HRID 432093 reaction equation
C(OC([N:8]([CH2:25][C@H:26]1[CH2:35][CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[C:31]([C:36]3[CH:45]=[CH:44][CH:43]=[CH:42][C:37]=3[C:38]([O:40][CH3:41])=[O:39])[CH:32]=2)[O:27]1)[CH2:9][C@H:10]([O:17][Si](C(C)(C)C)(C)C)[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=O)(C)(C)C.Cl>CO.O1CCOCC1>[OH:17][C@H:10]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[CH2:9][NH:8][CH2:25][C@H:26]1[CH2:35][CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[C:31]([C:36]3[CH:45]=[CH:44][CH:43]=[CH:42][C:37]=3[C:38]([O:40][CH3:41])=[O:39])[CH:32]=2)[O:27]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69733016HCID 69733016, compound

Product 1

HCID 59118229HCID 59118229, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A stirred solution of methyl 2-[(2R)-2-({(tert-butoxycarbonyl)[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-pyridinyl)ethyl]amino}methyl)-3,4-dihydro-2H-chromen-6-yl]benzoate (Example 82, 61 mg, 0.096 mmol) in MeOH (0.50 mL) was treated with HCl in dioxane (1 mL of a 4N solution in dioxane, Aldrich Chemical Co.) at room temperature and stirring continued for 60 minutes. The mixture was concentrated in vacuo and purified on silica gel using a gradient of 5-10% MeOH/EtOAc to provide 31 mg of product as colorless oil (77%); 1H NMR (DMSO-d6, δ): 1.65-2.04 (m, 2H), 2.50-3.10 (m, 6H), 3.65 (s, 3H), 4.10 (dd, 1H), 4.80 (d, 1H), 6.80 (d, 1H), 7.00 (bs, 2H), 7.25-7.40 (m, 3H), 7.42-7.52 (m, 1H), 7.78-7.80 (m, 2H), 8.52 (s, 1H), 8.60 (s, 1H); MS: m/z=419.3 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified on silica gel using a gradient of 5-10% MeOH/EtOAc

Sources & evidence

ORD record
ord-7fe797cd0cb74fd5948e5987d3200a69
Source dataset
uspto-grants-2003_12
Patent number
US06660752B2

Reaction notes

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