Hydrochloric Acid → (2R)-N-(Benzyloxy)-2-(hydroxymethyl)hexanamide

HRID 1396860Notes

Reaction equation

HRID 1396860 reaction equation
[OH:1][CH2:2][C@@H:3]([CH2:7][CH2:8][CH2:9][CH3:10])[C:4]([OH:6])=O.Cl.[CH2:12](NO)[C:13]1C=CC=C[CH:14]=1.Cl.CC[N:24]=C=NCCCN(C)C.[CH2:33]1[CH2:37][O:36][CH2:35][CH2:34]1.O>>[OH:1][CH2:2][C@@H:3]([CH2:7][CH2:8][CH2:9][CH3:10])[C:4]([NH:24][O:36][CH2:35][C:34]1[CH:33]=[CH:37][CH:14]=[CH:13][CH:12]=1)=[O:6]

Participants

6

Reactant 5

HCID 313Hydrochloric Acid2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 11332622N-benzylhydroxylamine hydrochlorideHCID 11550035(2R)-2-(hydroxymethyl)hexanoic AcidHCID 21881883Oxolane--water (1/1)

Product 1

HCID 16037944(2R)-N-(Benzyloxy)-2-(hydroxymethyl)hexanamide

Conditions

Temperature
0 °C

Procedure

To a 3000 mL roundbottom flask was added (2R)-2-(hydroxymethyl)hexanoic acid (5) (77 g, 0.527 mol) in THF/water (4:1, 1800 mL), followed by benzylhydroxylamine hydrochloride (100 g, 0.632 mol). The mixture was cooled to 0° C. and was adjusted with 1 N HCl to pH ˜4.5. EDCI (202 g, 1.05 mol) was added in one portion. The mixture was stirred at 0° C. for 2 h, while the pH of the mixture was maintained at ˜4.5 by addition of 1 N HCl. THF was then removed under vacuum, and the white solid was collected by filtration to afford the titled compound as a crude mixture (100 g). Further purification by flash column eluting with ethyl acetate/petroleum ether (1:10) provided the pure product (52 g, 39%). LCMS: (M+H)+: 252.2.

Workup

  1. customTHF was then removed under vacuum
  2. filtrationthe white solid was collected by filtration

Sources & evidence

ORD record
ord-00d96505fdd840b09741c6fc79a5d847
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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