Benzylamine → HCID 86590958, compound

HRID 1008271Notes

Reaction equation

[CH3:1][CH2:2][C@@H:3]([C:5]([O:7][C@@H:8]1[C@@H:13]2[C@@H:14]([CH2:19][CH2:20][C@H:21]3[O:27][C:25](=[O:26])[CH2:24][C@H:23]([OH:28])[CH2:22]3)[C@@H:15]([CH3:18])[CH:16]=[CH:17][C:12]2=[CH:11][C@H:10]([CH3:29])[CH2:9]1)=[O:6])[CH3:4].[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1(C)C=CC=CC=1>[CH3:1][CH2:2][C@@H:3]([C:5]([O:7][C@@H:8]1[C@@H:13]2[C@@H:14]([CH2:19][CH2:20][C@H:21]3[O:27][C:25](=[O:26])[CH2:24][C@H:23]([OH:28])[CH2:22]3)[C@@H:15]([CH3:18])[CH:16]=[CH:17][C:12]2=[CH:11][C@H:10]([CH3:29])[CH2:9]1)=[O:6])[CH3:4].[CH2:30]([NH-:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of Lovastatin (50 g, 0.124 mol) and benzylamine (46.32 g, 0.432 mol) was mixed with toluene (25 ml) and heated to 80° C. under nitrogen atmosphere for 1 hour. Absence of Lovastatin was monitored by HPLC. Excess benzylamine and toluene were distilled off at 85-90° C. under reduced pressure (5-10 mm Hg). The residue was mixed with xylenes (50 ml) and distilled again at 85-90° C. under reduced pressure (5-10 mm Hg) to get product, lovastatin benzylamide, as light brown viscous liquid. Yield: 67.5 g.

Workup

distillationExcess benzylamine and toluene were distilled off at 85-90° C. under reduced pressure (5-10 mm Hg)
additionThe residue was mixed with xylenes (50 ml)
distillationdistilled again at 85-90° C. under reduced pressure (5-10 mm Hg)

Sources & evidence

ORD record: ord-1fdab6946f5a4ab5afd3bedb4d440ab4
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06797831B2

Reaction notes

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