4-Nitrobenzyl alcohol → HCID 86749620, compound

HRID 1489841Notes

Reaction equation

HRID 1489841 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].O.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16]([OH:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1.[N+:21]([C:24]1[CH:31]=[CH:30][C:27]([CH2:28]O)=[CH:26][CH:25]=1)([O-:23])=[O:22]>C1C=CC=CC=1>[C:10]1([CH3:20])[CH:11]=[CH:12][C:13]([S:16]([OH:19])(=[O:17])=[O:18])=[CH:14][CH:15]=1.[N+:21]([C:24]1[CH:31]=[CH:30][C:27]([CH2:28][O:4][C:3](=[O:5])[C@@H:2]2[CH2:6][CH2:7][CH2:8][NH:1]2)=[CH:26][CH:25]=1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 692754-Nitrobenzyl alcoholHCID 145742L-ProlineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 86749620HCID 86749620, compoundYield 118.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture solution of 5.0 g of L-proline, 9.91 g of p-toluenesulfonic acid monohydrate and 6.65 g of p-nitrobenzyl alcohol in 100 ml of benzene was refluxed for 2 days by using Dean-Stark trap. After reaction, the solvent was removed under reduced pressure and the resulting residue was washed with diethyl ether to give 21.7 g of L-proline p-nitrobenzyl ester p-toluenesulfonic acid salt as oil. Then, a mixture solution of 12.17 g of Boc-glycine and 13.32 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide.hydrochloride in 150 ml of ethylene chloride was stirred for 25 minutes under ice-cooling at nitrogen atmosphere. To this reaction mixture was added a solution of 29.36 g of the compound obtained above in 100 ml ethylene chloride and the reaction mixture was stirred overnight at room temperature. After reaction, the reaction mixture was washed with 10% citric acid aqueous solution, 4% sodium bicarbonate aqueous solution and saline, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the resulting residue was purified by silica gel column chromatography (chloroform-methanol) to give 8.00 g of [N-(t-butoxycarbonyl)glycyl]L-proline p-nitrobenzyl ester [Compound (22)].

Workup

  1. customAfter reaction
  2. customthe solvent was removed under reduced pressure
  3. washthe resulting residue was washed with diethyl ether

Sources & evidence

ORD record
ord-ce79576293b240829315affeb9e1aeed
Source dataset
uspto-grants-1997_10
Patent number
US05679790

Reaction notes

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