5-[2-[(Butylamino)carbonyl]-3-methylbutyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester → Ammonium Hydroxide

HRID 1941350Notes

Reaction equation

HRID 1941350 reaction equation
[CH2:1]([NH:5][C:6]([CH:8]([CH:31]([CH3:33])[CH3:32])[CH2:9][CH:10]1[O:14]C(C)(C)[N:12](C(OC(C)(C)C)=O)[CH:11]1[CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:7])[CH2:2][CH2:3][CH3:4].[ClH:34].O1CCOCC1>>[NH4+:5].[OH-:7].[ClH:34].[NH2:12][CH:11]([CH2:24][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1)[CH:10]([OH:14])[CH2:9][CH:8]([CH:31]([CH3:32])[CH3:33])[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:7]

Participants

4

Reactant 2

HCID 147770545-[2-[(Butylamino)carbonyl]-3-methylbutyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl esterHCID 204431481,4-Dioxane hydrochloride

Product 2

HCID 14923Ammonium HydroxideHCID 19893258delta-Amino-N-butyl-gamma-hydroxy-alpha-(1-methylethyl)cyclohexanehexanamide hydrochloride

Procedure

5-[2-[(Butylamino)carbonyl]-3-methylbutyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester (171 mg, 0.366 mmol) was dissolved in an HCl/dioxane solution (1.37 mL, 4N HCl) at 0° C. and allowed to stand for two h. The solution was concentrated in vacuo. Silica gel chromatography (35:5:0.1 CH2Cl2 :MeOH:NH4OH) of the concentrate afforded the title compound as the free base (88.5 mg, 74%) which was subsequently converted to the hydrochloride salt. The free base was dissolved in MeOH (10 mL) and treated with 1N HCl (0.27 mL) for one h. The reaction was concentrated in vacuo, diluted with water, filtered and lyophilized to afford the title compound (72 mg, 54%).

Workup

  1. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-78c438d331f041169e03c78d23e7d03e
Source dataset
uspto-grants-1997_12
Patent number
US05703129

Reaction notes

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