HCID 70941355, compound → Di-tert-butyl (2R)-2-[(tert-butoxycarbonyl)amino]-5-(4-hydroxybenzyl)hexanedioate

HRID 591280Notes

Reaction equation

HRID 591280 reaction equation
[C:1]([O:5][C:6](=[O:37])[C@H:7]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:8][CH2:9][C:10]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)C(O)=O)([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1>[C:33]([O:32][C:30]([NH:29][C@H:7]([CH2:8][CH2:9][CH:10]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=1)[C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:37])=[O:31])([CH3:34])([CH3:35])[CH3:36]

Participants

3

Reactant 1

HCID 70941355HCID 70941355, compound

Product 1

HCID 117812675Di-tert-butyl (2R)-2-[(tert-butoxycarbonyl)amino]-5-(4-hydroxybenzyl)hexanedioateYield 65.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 237 mg (5R)-6-tert-butoxy-2-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)-amino]-2-(4-hydroxybenzyl)-6-oxohexanoic acid (0.45 mmol) and 94 mg 4-N,N-dimethylaminopyridine (0.77 mmol) in 1,4-dioxane (5 mL) was heated under reflux for 2 hours. The residue was purified by column chromatography on silica gel using an ethyl acetate/hexane gradient to give 141 mg of the title compound (65% yield).

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe residue was purified by column chromatography on silica gel using an ethyl acetate/hexane gradient

Sources & evidence

ORD record
ord-6d69d82d18ef4874b1c7f4f3bae0d03b
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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