Acetic Acid → (2S)-2-Amino-3-(4-(2-methoxycarbonyl-ethyl)-benzoylamino)-propionic acid tert-butyl ester

HRID 427307Notes

Reaction equation

HRID 427307 reaction equation
C(OC([NH:11][C@@H:12]([CH2:20][NH:21][C:22](=[O:35])[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:25][CH:24]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=O)C1C=CC=CC=1.C(O)(=O)C.[H][H]>CO.[Pd]>[C:16]([O:15][C:13](=[O:14])[C@@H:12]([NH2:11])[CH2:20][NH:21][C:22](=[O:35])[C:23]1[CH:24]=[CH:25][C:26]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:28]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 15512203tert-butyl (2S)-2-benzyloxycarbonylamino-3-(4-(2-methoxycarbonylethyl)benzoylamino)propionateHCID 178418361HCID 178418361, compound

Product 1

HCID 15550489(2S)-2-Amino-3-(4-(2-methoxycarbonyl-ethyl)-benzoylamino)-propionic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6.88 g (14.2 mmol) of tert-butyl (2S)-2-benzyloxycarbonylamino-3-(4-(2-methoxycarbonyl-ethyl)-benzoylamino)propionate was dissolved in 200 ml of methanol and 852 mg (14.2 mmol) of acetic acid was added. The mixture was hydrogenated for 7 hours at room temperature over Pd/C (5% strength) at 1 bar of hydrogen. The mixture was filtered and the solvent was removed in vacuo. The residue was washed with n-heptane and dried in vacuo. Yield 6.9 g. MS (ES+): m/e=351.2 (M+H+).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was removed in vacuo
  3. washThe residue was washed with n-heptane
  4. customdried in vacuo

Sources & evidence

ORD record
ord-4970964562b847f6a4c24eb89b7072a5
Source dataset
uspto-grants-2001_11
Patent number
US06313119B1

Reaction notes

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