Water → HCID 13967208, compound

Participants

Reaction Steps

To a stirred solution of 4-tert-butoxycarbonylamino-3-hydroxy-butyric acid (2.0 g) in dry DMF (30 ml) at room temperature was added K2CO3 (2.8 g). After 15 min. benzyl bromide (1.7 g) was added. After 16 h the mixture was poured into 200 ml of water and extracted into EtOAc (200 ml×2). The combined organics were washed with 1 N NaOH (40 ml); water (40 ml×2); brine (40 ml); dried over MgSO4; filtered, and concentrated under reduced pressure to give an oil. Purification by Flash 40 chromatography using a silica gel column and eluting with 30% EtOAc/hexane gave 2.1 g of the title compound as a colorless oil. 1H nmr (400 MHz, CDCl3) δ1.43 (s, 9H), 2.53 (m, 2H), 3.07-3.14 (m, 1H), 3.30-3.34 (m, 1H), 4.09-4.13 (m, 1H), 4.95 (broad s, 1H), 5.14 (s, 2H), 7.34 (m, 5H).

Provenance & Evidence