Benzyl Chloride → HCID 58636820, compound

HRID 1158948Notes

Reaction equation

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

Participants

Reactant 2

HCID 7503Benzyl Chloride

HCID 58636756HCID 58636756, compound

Product 1

HCID 58636820HCID 58636820, compoundYield 73%

Procedure

The coupling of 6-[tert-butoxycarbonyl-(3-hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-ylmethyl)-amino]-hexanoic acid (41) (3.0 g, 7.8 mmol) and benzyl chloride (7.0 g, 55 mmol), as described in Example 3, gave 6-[(3-benzyloxy-5-hydroxymethyl-2-methyl-pyridin-4-ylmethyl)-tert-butoxycarbonyl-amino]-hexanoic acid benzyl ester (42) (3.2 g, 73% yield).

Sources & evidence

ORD record: ord-ca5e500de6c6482e992151d0a94ad41c
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812037B2

Reaction notes

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