(Phenylmethoxy)acetaldehyde → HCID 117812711, compound

HRID 591336Notes

Reaction equation

HRID 591336 reaction equation
[NH2:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][CH:7]([CH2:15][CH2:16][C@H:17]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:4][CH:3]=1.[CH2:35]([O:42][CH2:43][CH:44]=O)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCCl>[CH2:35]([O:42][CH2:43][CH2:44][NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]([CH2:15][CH2:16][C@H:17]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])=[CH:33][CH:34]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 108989(Phenylmethoxy)acetaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 117812677HCID 117812677, compound

Product 1

HCID 117812711HCID 117812711, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Di-tert-butyl (5S)-2-(4-aminobenzyl)-5-[(tert-butoxycarbonyl)amino]hexanedioate (670 mg, 1.40 mmol) was dissolved in 1,2-dichloroethane (10 ml) and benzyloxyacetaldehyde (210 mg, 1.40 mmol) and sodium triacetoxyborohydride (415 mg, 1.96 mmol) were added. The mixture was stirred at room temperature for 4 h and than poured on 10 ml 1N aqueous sodium hydrogen carbonate solution. The aqueous phase was extracted with dichloromethane (2×10 ml) and the organic phases were washed with water (30 ml), dried over magnesium sulfate and concentrated in vacuo. Flash chromatography on silica gel (hexane, ethyl acetate) gave the product as slightly yellow oil (853 mg, 99%).

Workup

  1. extractionThe aqueous phase was extracted with dichloromethane (2×10 ml)
  2. washthe organic phases were washed with water (30 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8b1afc2502554a48858390a1ce602dc8
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

Loading…