Benzyl Chloride → HCID 86643603, compound

HRID 2381035Notes

Reaction equation

HRID 2381035 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][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[C:31]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:30]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]([O:20][C:21](=[O:24])[NH:22][CH3:23])[CH:7]=1.C([Cl:71])C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.CO.[Pd]>[Cl-:71].[CH2:13]([O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C@H:4]([NH:25][C:26]([C@@H:27]([NH3+:51])[CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[C:31]([O:43][CH2:44][C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH:30]=2)=[O:62])[C:3]([O:2][CH3:1])=[O:63])=[CH:7][C:8]=1[O:20][C:21](=[O:24])[NH:22][CH3:23])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 3

HCID 7503Benzyl ChlorideHCID 68724495HCID 68724495, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86643603HCID 86643603, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-2-[(S)-2-Benzyloxycarbonylamino-3-(3,4-bis-benzyloxy-phenyl)-propionylamino]-3-(4-benzyloxy-3-methylcarbamoyloxy-phenyl)-propionic acid methyl ester (0.95 g, 1.115 mmol) was suspended in ethyl acetate (20 ml) and methanol (20 ml). Pd/C (5%, 0.19 g) and benzyl chloride (0.155 g, 1.226 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 (3 ml) and diethyl ether was added and a white solid precipitated. (S)-1-[(S)-2-(4-Benzyloxy-3-methylcarbamoyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-(3,4-bis-benzyloxy-phenyl)-ethyl-ammonium chloride was obtained as white solid by filtration, 0.52 g. 1H NMR (400 MHz, d6-DMSO) 2.63 (d, 3H), 2.73 (m, 1H), 2.82-3.01 (m, 3H), 3.61 (s, 3H), 3.92 (m, 1H), 4.46 (m, 1H), 6.52 (m, 1H), 6.68 (m, 2H), 6.83-6.91 (m, 3H), 7.50 (m, 1H), 8.11 (br, 3H), 8.87 (s, 1H), 8.97 (s, 1H), 9.10 (d, J=7.6 Hz, 1H), 9.57 (s, 1H). m/z 448 (MH+). HPLC/MS (Method B) retention time 4.58 min, m/z 448 (MH+).

Workup

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

Sources & evidence

ORD record
ord-07e5088bd8b54003a3fc782bd2a02d32
Source dataset
uspto-grants-2012_09
Patent number
US08258097B2

Reaction notes

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