Benzyl Alcohol → HCID 86682257, compound

HRID 2363260Notes

Reaction equation

[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:11][C:12](=O)[C@H:13]([OH:31])[CH2:14][C@H:15]([NH2:30])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)=[CH:19][CH:18]=1)C.Cl.O1CCOCC1>>[CH2:1]([O:8][C:12](=[O:11])[C@H:13]([OH:31])[CH2:14][C@H:15]([NH2:30])[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)=[CH:21][CH:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 244Benzyl Alcohol

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 86682253(2R,4R)-4-amino-5-(3'-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester

Product 1

HCID 86682257HCID 86682257, compoundYield 101.3%

Conditions

Temperature: 60 °C

Procedure

Benzyl alcohol (13.0 mL, 126 mmol) was added to (2R,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester (1.9 g, 5.3 mmol) followed by 4.0 M HCl in 1,4-dioxane (5.3 mL, 21.3 mmol), and the mixture was stirred at 60° C. for 1 hour. The mixture was purified (Interchim reverse phase chromatography column; 30-90% MeCN in water with 0.05% TFA) to yield (2R,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxy-pentanoic acid benzyl ester (2.2 g) as a white solid. (evaporated in vacuo with water (4×300 mL) to remove excess benzyl alcohol).

Workup

customThe mixture was purified (Interchim reverse phase chromatography column; 30-90% MeCN in water with 0.05% TFA)

Sources & evidence

ORD record: ord-57317e1e0f25498ab870cdf336414401
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691868B2

Reaction notes

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