Benzyl Chloride → HCID 86643606, compound

HRID 2381038Notes

Reaction equation

HRID 2381038 reaction equation
[CH3:1][O:2][C:3](=[O:63])[C@@H:4]([NH:25][C:26](=[O:62])[C@@H:27]([NH:51]C(OCC1C=CC=CC=1)=O)[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35]CC2C=CC=CC=2)=[C:31]([O:43]CC2C=CC=CC=2)[CH:30]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13](=[O:16])[NH:14][CH3:15])=[C:8]([O:17]CC2C=CC=CC=2)[CH:7]=1.C([Cl:71])C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.CO.[Pd]>[Cl-:71].[OH:43][C:31]1[CH:30]=[C:29]([CH2:28][C@H:27]([NH3+:51])[C:26](=[O:62])[NH:25][C@H:4]([C:3]([O:2][CH3:1])=[O:63])[CH2:5][C:6]2[CH:11]=[CH:10][C:9]([O:12][C:13](=[O:16])[NH:14][CH3:15])=[C:8]([OH:17])[CH:7]=2)[CH:34]=[CH:33][C:32]=1[OH:35]

Participants

7

Reactant 3

HCID 7503Benzyl ChlorideHCID 68725422HCID 68725422, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86643606HCID 86643606, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-2-[(S)-2-Benzyloxycarbonylamino-3-(3,4-bis-benzyloxy-phenyl)-propionylamino]-3-(3-benzyloxy-4-methylcarbamoyloxy-phenyl)-propionic acid methyl ester (0.40 g, 0.470 mmol) was suspended in ethyl acetate (20 ml) and methanol (20 ml). Pd/C (5%, 0.10 g) and benzyl chloride (0.065 g, 0.517 mmol) were added. The hydrogenation was carried out under 30 psi of hydrogen for 3 h. After filtration and removal of solvent, the residue was redissolved in methanol (2 ml). Diethyl ether was added and a white solid precipitated. (S)-2-(3,4-Dihydroxy-phenyl)-1-[(S)-2-(3-hydroxy-4-methylcarbam-oyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-ethyl-ammonium chloride was obtained as a white solid by filtration, 0.22 g. 1H NMR (400 MHz, d6-DMSO) 2.63 (d, 3H), 2.72 (m, 1H), 2.83-3.02 (m, 3H), 3.64 (s, 3H), 3.93 (m, 1H), 4.50 (m, 1H), 6.52 (m, 1H), 6.65 (m, 3H), 6.85 (m, 2H), 7.46 (m, 1H), 8.11 (s, 3H), 8.87 (s, 1H), 8.96 (s, 1H), 9.13 (m, 1H), 9.61 (s, 1H). m/z 448 (MH+).

Workup

  1. filtrationAfter filtration and removal of solvent
  2. dissolutionthe residue was redissolved in methanol (2 ml)
  3. additionDiethyl ether was added
  4. customa white solid precipitated

Sources & evidence

ORD record
ord-32dd873cd4cb47898009e6d1f1024ad9
Source dataset
uspto-grants-2012_09
Patent number
US08258097B2

Reaction notes

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