Hydrochloric Acid → HCID 15594038, compound

HRID 346306Notes

Reaction equation

HRID 346306 reaction equation
[CH3:1][CH:2]([CH2:29][CH3:30])[CH2:3][NH:4][C:5](=[O:28])[CH2:6][CH:7]([O:21]C1CCCCO1)[CH:8]([NH:13]C(=O)OC(C)(C)C)[CH2:9][CH:10]([CH3:12])[CH3:11].Cl>ClCCl>[NH2:13][CH:8]([CH2:9][CH:10]([CH3:11])[CH3:12])[CH:7]([OH:21])[CH2:6][C:5]([NH:4][CH2:3][CH:2]([CH3:1])[CH2:29][CH3:30])=[O:28]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14651694HCID 14651694, compound

Product 1

HCID 15594038HCID 15594038, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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).

Workup

  1. customThe mixture is evaporated
  2. customthe resulting gum is partitioned between diethyl ether and 0.5N hydrochloric acid solution
  3. customThe aqueous layer is separated
  4. extractionextracted with diethyl ether (5×100 ml)
  5. dry with materialThe combined organic extracts are dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-c9773e6dc1ae4ffc83261f172d488996
Source dataset
uspto-grants-1991_10
Patent number
US05061808

Reaction notes

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