Hydrochloric Acid → HCID 20165900, compound

HRID 346307Notes

Reaction equation

HRID 346307 reaction equation
[NH2:1][CH:2]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH:3]([OH:13])[CH2:4][C:5]([NH:7][CH2:8][CH:9]([CH3:12])[CH2:10][CH3:11])=[O:6].[ClH:18]>CO>[ClH:18].[NH2:1][CH:2]([CH2:14][CH:15]([CH3:16])[CH3:17])[CH:3]([OH:13])[CH2:4][C:5]([NH:7][CH2:8][CH:9]([CH3:12])[CH2:10][CH3:11])=[O:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15594038HCID 15594038, compound

Product 1

HCID 20165900HCID 20165900, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3 g (7 mmol) of a mixture of [1S-[1R*,2R*(R*),4(R*)]] and [1S-[1R*,2R*(S*),4(R*)]][4-[(2-methylbutyl)amino]-1-(2-methylpropyl)-4-oxo-2-[(tetrahydro-2H-pyran-2-yl)oxy] butyl]carbamic acid, 1,1-dimethylethyl ester in 75 ml of dichloromethane is treated with 25 ml of methanolic hydrogen chloride solution and stirred at room temperature for 2 hours. The mixture is evaporated and the resulting gum is partitioned between diethyl ether and 0.5N hydrochloric acid solution. The aqueous layer is separated, basified to pH 13 with a 2N solution of sodium hydroxide and extracted with diethyl ether (5×100 ml). The combined organic extracts are dried over magnesium sulfate and evaporated to give 1.64 g of [3S-[N(R*),3R*,4R*]]-4-amino-3-hydroxy-6-methyl-N(2-methylbutyl)-heptanamide; [α]D23 =-22.2° (C=1.07%, methanol). Reaction of [3S-[N(R*),3R*,4R*]]-4-amino-3-hydroxy-6-methyl -N(2-methylbutyl)-heptanamide with hydrogen chloride gas in the conventional manner affords [3S-[N(R*),3R*,4R*]]-4-amino-3-hydroxy-6-methyl-N(2-methylbutyl)-heptanamide, hydrochloride (2:3).

Sources & evidence

ORD record
ord-8890ede4b0f943fb956f8c7ee74bc1a0
Source dataset
uspto-grants-1991_10
Patent number
US05061808

Reaction notes

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