Benzyl Alcohol → HCID 69940123, compound

HRID 1058775Notes

Reaction equation

HRID 1058775 reaction equation
[OH:1][P:2]([CH2:20][CH:21]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:22]([NH:24][C@H:25]([C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:23])([CH:4]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH2:50](O)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C>O1CCCC1>[C:6]1([CH2:5][CH:4]([P:2]([CH2:20][CH:21]([CH2:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:22]([NH:24][C@H:25]([C:33]([O:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[O:34])[CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:23])([O:1][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[O:3])[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 69939850HCID 69939850, compound

Product 1

HCID 69940123HCID 69940123, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenylmethyl N-[2-[[hydroxy[2-phenyl-1-[[(tert-butoxy)carbonyl]amino]ethyl]phosphinyl]methyl]-1-oxo-3-phenylpropyl]-L-phenylalaninate is treated with benzyl alcohol (1.1 eq.) in the presence of dicyclohexylcarbodiimide and dimethylaminopyridine in tetrahydrofuran. After stirring overnight at room temperature, the mixture is filtered and then evaporated to dryness. The residue is taken up in ethyl acetate. This solution is washed 3 times with water, dried over sodium sulphate and then evaporated to dryness. The product is purified by chromatography on silica gel, eluting with a 1/9 dichloromethane/methanol mixture. The product is recovered in a yield of 60%.

Workup

  1. filtrationthe mixture is filtered
  2. customevaporated to dryness
  3. washThis solution is washed 3 times with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated to dryness
  6. customThe product is purified by chromatography on silica gel
  7. washeluting with a 1/9 dichloromethane/methanol mixture
  8. customThe product is recovered in a yield of 60%

Sources & evidence

ORD record
ord-260535520fe14120a7f52058a7c865b7
Source dataset
uspto-grants-2003_02
Patent number
US06518260B1

Reaction notes

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