Hydrochloric Acid → Benzyl-[(1R)-2-(D-alanylamino)-1-benzylethyl]carbamate

HRID 1849987Notes

Reaction equation

HRID 1849987 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:10][NH:11][C:12](=[O:26])[C@H:13]([NH:15]C(=O)OCC1C=CC=CC=1)[CH3:14])=[O:7])([CH3:4])(C)C.Cl>O1CCOCC1>[CH2:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH2:10][NH:11][C:12](=[O:26])[C@@H:13]([CH3:14])[NH2:15])[C:4]1[CH:29]=[CH:28][CH:27]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86717649Benzyl [(1R)-2-({(2R)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl}amino)-1-methyl-2-oxoethyl]carbamate

Product 1

HCID 71229500Benzyl-[(1R)-2-(D-alanylamino)-1-benzylethyl]carbamateYield 114.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Benzyl [(1R)-2-({(2R)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl}amino)-1-methyl-2-oxoethyl]carbamate (335 mg, 0.74 mmol) was dissolved in 5 mL dioxane and hydrogen chloride (4M solution in dioxane, 5 mL, 20 mmol) added and the mixture stirred at room temperature for 16 h. The mixture was evaporated under reduced pressure and the residue purified by flash column chromatography eluting with a 9:1 mixture of dichloromethane in methanol to give 150 mg (63%) of the title compound as a waxy white solid.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customthe residue purified by flash column chromatography
  3. washeluting with a 9:1 mixture of dichloromethane in methanol

Sources & evidence

ORD record
ord-b7a545e47ecc41debe748720e109df30
Source dataset
uspto-grants-2015_02
Patent number
US08957025B2

Reaction notes

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