Hydrochloric Acid → N-Glycyl-3(R)-methyl-beta-alanine benzyl ester hydrochloride

HRID 862436Notes

Reaction equation

HRID 862436 reaction equation
[CH2:1]([O:8][C:9](=[O:25])[CH2:10][C@@H:11]([CH3:24])[NH:12][C:13](=[O:23])[CH2:14][NH:15]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:26]>CCOC(C)=O>[ClH:26].[CH2:1]([O:8][C:9](=[O:25])[CH2:10][C@@H:11]([CH3:24])[NH:12][C:13](=[O:23])[CH2:14][NH2:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86751222N-t-Butoxycarbonylglycyl-3(R)-methyl-beta-alanine benzyl ester

Product 1

HCID 86751220N-Glycyl-3(R)-methyl-beta-alanine benzyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-t-Butoxycarbonylglycyl-3(R)-methyl-β-alanine benzyl ester 2-4 (3.32 g) in EtOAc (100 mL) cooled to -60° C. was treated with HCl gas until saturated. The mixture was stirred for 30 minutes then the solvent was removed and the residue triturated with ether to give 2-5 as a solid. ##STR59## N-{[6-Nitro-2,3-dihydro-1(1H)-isoindolone-2-yl]acetyl}-3(R)-methyl-β-alanine benzyl ester (2-6)

Workup

  1. customthe solvent was removed
  2. customthe residue triturated with ether

Sources & evidence

ORD record
ord-e82bf3e0485d494c95d6c4ab3132c5bb
Source dataset
uspto-grants-1998_02
Patent number
US05719144

Reaction notes

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