(2R,3S)-2-(tert-butoxy-carbonylamino)-3-hydroxy-4,4-dimethyl-pentanoate → (2R,3S)-2-Amino-3-Hydroxy-4,4-Dimethylpentanoic Acid

HRID 530570Notes

Reaction equation

C(OC([NH:8][C@H:9]([C@@H:13]([OH:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[C:10]([O-:12])=[O:11])=O)(C)(C)C>Cl>[NH2:8][C@H:9]([C@@H:13]([OH:18])[C:14]([CH3:16])([CH3:15])[CH3:17])[C:10]([OH:12])=[O:11]

Participants

Conditions

Temperature: 130 °C

Procedure

In a round-bottomed flask, the diastereomeric mixture containing (2R*,3R*)- and (2R*,3S*)-2-(tert-butoxy-carbonylamino)-3-hydroxy-4,4-dimethyl-pentanoate (0.4 g, 1.38 mmol) was dissolved in a 6.0 M HCl solution (30 mL). The resulting solution was divided into two equal aliquots and stirred at 130° C. for 1 h. All portions were joined and the reaction mixture extracted with Et2O (3×20 mL). The aqueous phase was concentrated under reduced pressure giving a yellowish solid crude product, as a diastereoisomeric mixture (anti:syn=9:1), which was used without further purification in the following step. MS (ESI) m/z: 162 [M−H]+; (ESI) m/z: 160 [M−H]−.

Workup

extractionthe reaction mixture extracted with Et2O (3×20 mL)
concentrationThe aqueous phase was concentrated under reduced pressure
customgiving a yellowish solid crude product
customas a diastereoisomeric mixture (anti:syn=9:1), which was used without further purification in the following step

Sources & evidence

ORD record: ord-e4a01ff4bb8f4180a10213d928f663a6
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353075B2

Reaction notes

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