Hydrochloric Acid → HCID 86606484, compound

HRID 2055198Notes

Reaction equation

HRID 2055198 reaction equation
C[O:2][C:3]([C:5]1([CH:13]=[N:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][C@H:9]([CH3:11])[CH2:8][C@H:7]([CH3:12])[CH2:6]1)=[O:4].O.[OH-].[Li+].Cl>C1COCC1.O>[CH2:16]([O:15][N:14]=[CH:13][C:5]1([C:3]([OH:4])=[O:2])[CH2:10][C@H:9]([CH3:11])[CH2:8][C@H:7]([CH3:12])[CH2:6]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86606483HCID 86606483, compound

Product 1

HCID 86606484HCID 86606484, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (3S,5R)-1-(benzyloxyimino-methyl)-3,5-dimethyl-cyclohexanecarboxylic acid methyl ester (4.8 g, 15.8 mmol) and lithium hydroxide monohydrate (6.6 g, 158 mmol) in THF (170 mL) and water (85 mL) was heated at 90° C. for 48 h. The reaction mixture was acidified to pH 3 with 6N aqueous HCl and was extracted with dichloromethane (75 mL×6). The combined organic layers were dried (MgSO4) and were evaporated in vacuo to yield the title compound as a pale yellow oil. (1.8 g, 39%). MH+290.

Workup

  1. extractionwas extracted with dichloromethane (75 mL×6)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-c7514154563f44afa0169b9b11aa389a
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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